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163222-32-0

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2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-, (3R,4S)-
Cas No: 163222-32-0
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(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone Manufacturer/High quality/Best price/In stock
Cas No: 163222-32-0
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-Fluorophenyl)-3-Hydroxypropyl]-4-[4-(Phenylmethoxy)Phenyl]-2-Azetidinone supplier in China
Cas No: 163222-32-0
No Data 1 Metric Ton 30 Metric Ton/Month Simagchem Corporation Contact Supplier
Factory Supply (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-Fluorophenyl)-3-Hydroxypropyl]-4-[4-(Phenylmethoxy)Phenyl]-2-Azetidinone
Cas No: 163222-32-0
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163222-32-0 2-AZETIDINONE, 1-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL]-4-[4-(PHENYLMETHOXY)PHENYL]-, (3R,4S)-
Cas No: 163222-32-0
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High Quality 99% (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone 163222-32-0 GMP manufacturer
Cas No: 163222-32-0
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
TIANFU CHEM--2-AZETIDINONE, 1-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL]-4-[4-(PHENYLMETHOXY)PHENYL]-, (3R,4S)-
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New production CAS 163222-32-0 with best quality
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BLOOM TECH Advanced API/Technology support (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)azetidin-2-one CAS 163222-32-0
Cas No: 163222-32-0
No Data 1 Gram 3 Metric Ton/Month Shaanxi BLOOM TECH Co.,Ltd Contact Supplier
(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone 163222-32-0
Cas No: 163222-32-0
No Data 1 Kilogram 10000 Metric Ton/Month Shanghai Upbio Tech Co.,Ltd Contact Supplier

163222-32-0 Usage

Chemical Properties

Off-White Solid

Uses

(3R,4S)-4-(4-(Benzyloxy)Phenyl)-1-(4-Fluorophenyl)-3-((S)-3-(4-Fluorophenyl)-3-Hydroxypropyl)Azetidin-2-One is protected Ezetimibe, used for the synthesis of related derivatives.
InChI:InChI=1/C31H27F2NO3/c32-24-10-6-22(7-11-24)29(35)19-18-28-30(34(31(28)36)26-14-12-25(33)13-15-26)23-8-16-27(17-9-23)37-20-21-4-2-1-3-5-21/h1-17,28-30,35H,18-20H2/t28-,29+,30-/m1/s1

163222-32-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4'-O-Benzyloxy Ezetimibe

1.2 Other means of identification

Product number -
Other names 2-AZETIDINONE, 1-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL]-4-[4-(PHENYLMETHOXY)PHENYL]-, (3R,4S)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:163222-32-0 SDS

163222-32-0Synthetic route

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With formic acid; [(S,S)-teth-TsDpen RuCl]; triethylamine In ethylbenzene at 35 - 40℃; for 24h; Inert atmosphere;99.8%
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; methyl tertiarybutylether; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity;98.04%
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity;98.6%
benzyl bromide
100-39-0

benzyl bromide

ezetemibe
163222-33-1

ezetemibe

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;99%
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

A

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

B

(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one
163380-15-2

(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h;A 0.141 g
B n/a
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h;
Stage #1: (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 19 - 22℃; for 2.78333h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 2℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Overall yield = 99 %; enantioselective reaction;A n/a
B n/a
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Optical yield = 85 percent ee; enantioselective reaction;
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C
2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
3: BF3 etherate / toluene / 0.08 h / -30 °C
4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
6: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C
2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux
3: formic acid / dichloromethane / 12 h / Reflux
4: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C
View Scheme
Multi-step reaction with 2 steps
1: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C
2: dimethylsulfide borane complex / dichloromethane; toluene / 3 h / -5 - 0 °C / Inert atmosphere
View Scheme
(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde
221349-58-2

(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one
221349-56-0

(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
2: BF3 etherate / toluene / 0.08 h / -30 °C
3: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
4: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
5: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
lithium; 1-(4-fluoro-phenyl)-ethenolate

lithium; 1-(4-fluoro-phenyl)-ethenolate

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one
221349-60-6

(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
2: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one
231301-00-1

(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
2: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
3: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine
219653-96-0

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: (nBu)3N / heptane; toluene / 80 - 90 °C
2: LiOH*H2O / methanol / 2 h
3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
5: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
3: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
204589-84-4

3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
2: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
204589-80-0

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiOH*H2O / methanol / 2 h
2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
4: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
Multi-step reaction with 3 steps
1.1: diethyl aluminiumcholoride / toluene / -12 - 20 °C / Inert atmosphere
2.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere
2.2: 1 h / -5 - 0 °C
3.1: [(S,S)-teth-TsDpen RuCl]; triethylamine; formic acid / ethylbenzene / 24 h / 35 - 40 °C / Inert atmosphere
View Scheme
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Stage #1: [14C]-Sch 57871; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: With dimethylsulfide borane complex In tetrahydrofuran at -20℃; for 1.5h;
1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-3(R)-(3-oxo-3-phenylpropyl)-2-azetidinone
163222-31-9

1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-3(R)-(3-oxo-3-phenylpropyl)-2-azetidinone

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -20℃; for 1.5h;
methanol
67-56-1

methanol

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran
1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium; Bis<2-(N,N-dimethylamino)aethyl>aether / 0.5 h / 0 °C
2.1: (R)-1,1'-Bi-2-naphthol / titanium(IV) isopropylate / diethyl ether; tetrahydrofuran / 1.5 h / 0 - 25 °C
2.2: -20 - 25 °C
2.3: 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere
1.2: 1 h / -5 - 0 °C
2.1: [(S,S)-teth-TsDpen RuCl]; triethylamine; formic acid / ethylbenzene / 24 h / 35 - 40 °C / Inert atmosphere
View Scheme
3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal
1412967-16-8

3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Stage #1: 4-flourophenylmagnesium bromide With (R)-1,1'-Bi-2-naphthol; titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 25℃; for 1.5h;
Stage #2: 3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal In tetrahydrofuran; diethyl ether at -20 - 25℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0℃;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate; sodium hypochlorite; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / Difluoromethane / 25 °C / Cooling with ice
2.1: (R)-1,1'-Bi-2-naphthol / titanium(IV) isopropylate / diethyl ether; tetrahydrofuran / 1.5 h / 0 - 25 °C
2.2: -20 - 25 °C
2.3: 0 °C
View Scheme
(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one
1416263-33-6

(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; water / 18 h
2: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
3: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(1'S,3R,6S)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one
1416263-36-9

(1'S,3R,6S)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In diethyl ether at 0℃; for 2h;
(3S,3aS,6S,7aS)-3-(4-(benzyloxy)phenyl)-2,6-bis(4-fluorophenyl)tetrahydro-2H-pyrano[3,4-d]isoxazol-4(6H)-one
1416263-37-0

(3S,3aS,6S,7aS)-3-(4-(benzyloxy)phenyl)-2,6-bis(4-fluorophenyl)tetrahydro-2H-pyrano[3,4-d]isoxazol-4(6H)-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
2: Burgess Reagent / toluene / 18 h / 90 °C
3: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
4: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(R)-2,3-dihydro-2-(4-fluorophenyl)-4H-pyran-4-one

(R)-2,3-dihydro-2-(4-fluorophenyl)-4H-pyran-4-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4: toluene / 72 h / Reflux
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
7: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
8: Burgess Reagent / toluene / 18 h / 90 °C
9: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
10: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
7: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
8: Burgess Reagent / toluene / 18 h / 90 °C
9: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
10: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4.1: toluene / 72 h / Reflux
5.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
6.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
6.2: 0.25 h / 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 18 h
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
9.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
5.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
6.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
6.2: 0.25 h / 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 18 h
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
9.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(3S,4S,6S)-3-((S)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)methyl)-6-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-one

(3S,4S,6S)-3-((S)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)methyl)-6-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Burgess Reagent / toluene / 18 h / 90 °C
2: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
3: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(6S)-3-((R)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)-methyl)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one
1416263-38-1

(6S)-3-((R)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)-methyl)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
2: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: toluene / 72 h / Reflux
6.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
7.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
7.2: 0.25 h / 20 °C
8.1: lithium hydroxide / tetrahydrofuran; water / 18 h
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
10.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
6.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
7.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
7.2: 0.25 h / 20 °C
8.1: lithium hydroxide / tetrahydrofuran; water / 18 h
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
10.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: toluene / 72 h / Reflux
6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
8.1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
9.1: Burgess Reagent / toluene / 18 h / 90 °C
10.1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
11.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
8.1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
9.1: Burgess Reagent / toluene / 18 h / 90 °C
10.1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
11.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol
1416263-27-8

(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / 12 h / 20 °C
1.2: 4 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C
3.1: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux
4.1: formic acid / dichloromethane / 12 h / Reflux
5.1: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C
View Scheme
benzyl chloride
100-44-7

benzyl chloride

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: methanesulfonic acid / acetone / 2 h / 20 °C
2.1: toluene / 72 h / Reflux
3.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
4.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
4.2: 0.25 h / 20 °C
5.1: lithium hydroxide / tetrahydrofuran; water / 18 h
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
7.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanesulfonic acid / acetone / 2 h / 20 °C
2.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
3.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
4.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
4.2: 0.25 h / 20 °C
5.1: lithium hydroxide / tetrahydrofuran; water / 18 h
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
7.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: methanesulfonic acid / acetone / 2 h / 20 °C
2: toluene / 72 h / Reflux
3: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
5: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
6: Burgess Reagent / toluene / 18 h / 90 °C
7: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
8: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; cyclohexane at 70℃; under 760.051 Torr; for 3h;99%
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50 - 55℃; under 37.5038 - 75.0075 Torr;90.3%
With palladium 10% on activated carbon; ammonium formate; acetic acid for 6h; Reflux;90%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

(1S)-3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl (2S)-2-{[(tert-butoxy)carbonyl]amino}propanoate

(1S)-3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl (2S)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;69%
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

1-(4-fluorophenyl)-(3R)-[(4-fluorophenyl)-(2E)-propenyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone

1-(4-fluorophenyl)-(3R)-[(4-fluorophenyl)-(2E)-propenyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
2: p-TsOH*H2O / toluene / 6 h / 80 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone
163380-20-9

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
2: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

A

EZT-FAM
1197811-72-5

EZT-FAM

B

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With formic acid; ammonium formate; 5%-palladium/activated carbon In methanol at 20℃; Product distribution / selectivity; Inert atmosphere;
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