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(5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione is a complex organic compound with a unique molecular structure. It is characterized by its fluorinated phenyl and morpholinyl groups, which contribute to its chemical properties and potential applications in various fields.

168828-82-8

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168828-82-8 Usage

Uses

Used in Pharmaceutical Industry:
(5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione is used as an intermediate in the synthesis of Linezolid Dimer (L466520), which is an impurity of the antibacterial agent Linezolid (L466500). (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione plays a crucial role in the development and production of effective antibacterial drugs, contributing to the fight against bacterial infections and resistance.

Check Digit Verification of cas no

The CAS Registry Mumber 168828-82-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,8,8,2 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 168828-82:
(8*1)+(7*6)+(6*8)+(5*8)+(4*2)+(3*8)+(2*8)+(1*2)=188
188 % 10 = 8
So 168828-82-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H17FN2O4/c15-12-7-10(17-8-11(9-18)21-14(17)19)1-2-13(12)16-3-5-20-6-4-16/h1-2,7,11,18H,3-6,8-9H2/t11-/m1/s1

168828-82-8SDS

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 (R)-3-(3-Fluoro-4-morpholinophenyl)-5-(hydroxymethyl)oxazolidin-2-one

1.2 Other means of identification

Product number -
Other names (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

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:168828-82-8 SDS

168828-82-8Synthetic route

((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester
912552-56-8

((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;96%
(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water
85.1%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium; butan-1-ol In tetrahydrofuran; hexane at -15 - 30℃; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -10 - 15℃;
Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate
85%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.63333h;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 22.1h;
83%
carbon dioxide
124-38-9

carbon dioxide

(S)-N-(2,3-epoxy-1-propyl)-3-fluoro-4-(4-morpholinyl)aniline

(S)-N-(2,3-epoxy-1-propyl)-3-fluoro-4-(4-morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With dmap; C20H14AlNO3 In dichloromethane at 25℃; under 760.051 Torr; for 60h; Sealed tube; stereoselective reaction;85%
N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline
565176-83-2

N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline

(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3.5h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at 20℃; for 0.5h; Product distribution / selectivity;
80%
N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline
903593-93-1

N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline With hydrogenchloride; water In methanol at 20℃; for 8h;
Stage #2: bis(trichloromethyl) carbonate With sodium carbonate at 20℃; for 24h; Further stages.;
56%
(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-carbaldehyde-2-oxazolidinone

(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-carbaldehyde-2-oxazolidinone

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; Yield given;
(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multistep reaction;
3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. NaHCO3 / acetone
2.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
3.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
3.2: NaBH4 / methanol
3.3: 86 percent / CuSO4 / methanol
4.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester
912552-55-7

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
1.2: NaBH4 / methanol
1.3: 86 percent / CuSO4 / methanol
2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester
912552-54-6

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
2.2: NaBH4 / methanol
2.3: 86 percent / CuSO4 / methanol
3.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaI; Na2CO3 / dimethylformamide / 65 °C
2.1: aq. NaHCO3 / acetone
3.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
4.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
4.2: NaBH4 / methanol
4.3: 86 percent / CuSO4 / methanol
5.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: NaHCO3
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 70 percent / sodium bicarbonate / acetone; H2O
2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
3,4-difluoronitrobenzene
369-34-6

3,4-difluoronitrobenzene

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N,N-diisopropylethylamine
2.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran
3.1: NaHCO3
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-diisopropylethylamine / acetonitrile / 17 h / Heating
2: H2 / PtO2 / methanol / 3 h / 20 °C / 1471.02 Torr
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / N,N-diisopropylethylamine / ethyl acetate
2: ammonium formate / 10percent Pd/C
3: 70 percent / sodium bicarbonate / acetone; H2O
4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
3-fluoro-4-(4-morpholinyl)nitrobenzene
2689-39-6

3-fluoro-4-(4-morpholinyl)nitrobenzene

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran
2.1: NaHCO3
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: hexane; tetrahydrofuran / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2 / PtO2 / methanol / 3 h / 20 °C / 1471.02 Torr
View Scheme
Multi-step reaction with 3 steps
1: ammonium formate / 10percent Pd/C
2: 70 percent / sodium bicarbonate / acetone; H2O
3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h
View Scheme
(R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol
905945-96-2

(R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CH2Cl2 / Ambient temperature
2: 2N HCl / Ambient temperature
3: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
4: NaBH4 / methanol / 0 °C
View Scheme
C28H32F2N4O8
239438-43-8

C28H32F2N4O8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
2: NaBH4 / methanol / 0 °C
View Scheme
C31H36F2N4O8
239438-39-2

C31H36F2N4O8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N HCl / Ambient temperature
2: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C
3: NaBH4 / methanol / 0 °C
View Scheme
N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline
868405-66-7

N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C
2: N,N-dimethyl-formamide / 120 °C
3: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 24 h / 25 - 30 °C
2: N,N-dimethyl-formamide / 120 °C
3: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 120 °C
2: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 120 °C
2: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C
View Scheme
(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate
496031-56-2

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With water; sodium t-butanolate In tetrahydrofuran at 0 - 15℃; for 0.5h;
With water; sodium t-butanolate In tetrahydrofuran at 0 - 15℃; for 0.5h;50 g
(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With potassium tert-butylate; lithium diisopropyl amide
(2R)-1-chloro-3-{[3-fluoro-4-(morpholin-4-yl)phenyl]amino}-propan-2-ol

(2R)-1-chloro-3-{[3-fluoro-4-(morpholin-4-yl)phenyl]amino}-propan-2-ol

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / dichloromethane; water / 24 h
2: dmap; C20H14AlNO3 / dichloromethane / 60 h / 25 °C / 760.05 Torr / Sealed tube
View Scheme
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-methyl methanesulfonate
174649-09-3

(R)-methyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.5h;100%
With triethylamine In tetrahydrofuran at 8 - 15℃; for 3.75h; Cooling with ice; Inert atmosphere;96%
With triethylamine In dichloromethane at 20 - 30℃;95%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate
168828-83-9

(R)-[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;92%
With triethylamine In dichloromethane at 0 - 20℃; for 18.8333h;92%
With triethylamine In dichloromethane at 0 - 20℃; for 18h;85%
4-iodobenzenesulfonyl chloride
98-61-3

4-iodobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-iodobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-iodobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;82.5%
4-bromobenzenesulfonyl chloride
98-58-8

4-bromobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-bromobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-bromobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 26h;81.5%
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

thioacetic acid
507-09-5

thioacetic acid

linezolid
165800-03-3

linezolid

Conditions
ConditionsYield
Stage #1: (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol With methanesulfonyl chloride
Stage #2: With sodium azide
Stage #3: tiolacetic acid stereoselective reaction;
81%
4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-fluorobenzenesulfonate

(R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-fluorobenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h;80.3%
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one
168828-84-0

(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃;
Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; Further stages.;
79%
Multi-step reaction with 2 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
View Scheme
Multi-step reaction with 2 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
View Scheme
acetic anhydride
108-24-7

acetic anhydride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate
496031-56-2

(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 4h;75%
isoxazol-3-ol
5777-20-8

isoxazol-3-ol

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

5(R)-Isoxazol-3-yloxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one
252260-22-3

5(R)-Isoxazol-3-yloxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran69%
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester
198410-26-3

4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

Conditions
ConditionsYield
With triethylamine
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine
168828-90-8

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
3: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: Et3N
2: NH3 / methanol
View Scheme
Multi-step reaction with 3 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

linezolid
165800-03-3

linezolid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / CH2Cl2 / 4 h / 0 °C
2: NaN3 / dimethylformamide / 75 °C
3: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
4: pyridine
View Scheme
Multi-step reaction with 3 steps
1: Et3N
2: NH3 / methanol
3: 2 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Et3N
2: NaN3 / dimethylsulfoxide / 80 °C
3: 86 percent / Ambient temperature
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(R)-[{N-3-(3-fluoro-4-morpholinophenyl)-2-oxo-oxazolidin-5-yl}methyl]isothiocyanate
216869-07-7

(R)-[{N-3-(3-fluoro-4-morpholinophenyl)-2-oxo-oxazolidin-5-yl}methyl]isothiocyanate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Et3N / tetrahydrofuran / 2 h / 20 °C
2.1: sodium azide / dimethylformamide / 6 h / 65 °C
3.1: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4.1: Et3N / tetrahydrofuran / 4 h / 0 °C
4.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methyldithiocarbamate
216868-96-1

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methyldithiocarbamate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4: Et3N / tetrahydrofuran / 7 h / 0 °C
5: Et3N / tetrahydrofuran / 0.5 h / 20 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea

(S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: Et3N / tetrahydrofuran / 2 h / 20 °C
2.1: sodium azide / dimethylformamide / 6 h / 65 °C
3.1: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4.1: Et3N / tetrahydrofuran / 4 h / 0 °C
4.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C
5.1: 40 percent / NH3 / methanol / 3 h / 0 °C
View Scheme
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

[(S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-dithiocarbamic acid

[(S)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-dithiocarbamic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / tetrahydrofuran / 2 h / 20 °C
2: sodium azide / dimethylformamide / 6 h / 65 °C
3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C
4: Et3N / tetrahydrofuran / 7 h / 0 °C
View Scheme

168828-82-8Relevant articles and documents

Synthesis of covalent bonding MWCNT-oligoethylene linezolid conjugates and their antibacterial activity against bacterial strains

Alatorre-Barajas, José A.,Alcántar-Zavala, Eleazar,Alonso-Nú?ez, Gabriel,Cabrera, Alberto,Estrada-Zavala, Edgar,Gil-Rivas, M. Graciela,Gochi-Ponce, Y.,Medina-Franco, J. L.,Montes-ávila, Julio,Ochoa-Terán, Adrián,Reynoso-Soto, Edgar A.,Rivera-Lugo, Yazmin Yorely,Trujillo-Navarrete, Balter

, p. 28912 - 28924 (2021/09/22)

Nowadays, infectious diseases caused by drug-resistant bacteria have become especially important. Linezolid is an antibacterial drug active against clinically important Gram positive strains; however, resistance showed by these bacteria has been reported. Nanotechnology has improved a broad area of science, such as medicine, developing new drug delivery and transport systems. In this work, several covalently bounded conjugated nanomaterials were synthesized from multiwalled carbon nanotubes (MWCNTs), a different length oligoethylene chain (Sn), and two linezolid precursors (4and7), and they were evaluated in antibacterial assays. Interestingly, due to the intrinsic antibacterial activity of the amino-oligoethylene linezolid analogues, these conjugated nanomaterials showed significant antibacterial activity against various tested bacterial strains in a radial diffusion assay and microdilution method, including Gram negative strains asEscherichia coli(11 mm, 6.25 μg mL?1) andSalmonella typhi(14 mm, ≤0.78 μg mL?1), which are not inhibited by linezolid. The results show a significant effect of the oligoethylene chain length over the antibacterial activity. Molecular docking of amino-oligoethylene linezolid analogs shows a more favorable interaction of theS2-7analog in the PTC ofE. coli.

Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2

Lee, Yuseop,Choi, Jonghoon,Kim, Hyunwoo

, p. 5036 - 5039 (2018/08/24)

A divergent coupling reaction was achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A gram-scale production of Linezolid was successfully achieved.

A kind of linezolid intermediate, preparation method thereof, and method for preparing and enduring zolamide

-

, (2017/04/04)

The invention discloses a novel Linezolid intermediate, its preparation method and a novel preparation method of Linezolid, a structure of the Linezolid key intermediate is shown as a formula (I), in the formula (I), X is fluorine, chlorine, bromine or iodine. According to the invention, the Linezolid intermediate solves the problems of poor solubility of the Linezolid intermediate, and low yield and purity of the synthesized Linezolid in the prior art. The preparation methods of the invention have the advantages of easy preparation process, easy raw material acquisition, low cost, easy purification of intermediate product and final product, high yield and purity, and are suitable for large-scale industrial production.

Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives

Phillips, Oludotun A.,D'Silva, Roselyn,Bahta, Teklu O.,Sharaf, Leyla H.,Udo, Edet E.,Benov, Ludmil,Eric Walters

, p. 120 - 131 (2015/11/24)

Research activities on the oxazolidinone antibacterial class of compounds continue to focus on developing newer derivatives with improved potency, broad-spectrum activity and safety profiles superior to linezolid. Among the safety concerns with the oxazolidinone antibacterial agents is inhibition of monoamine oxidases (MAO) resulting from their structural similarity with toloxatone, a known MAO inhibitor. Diverse substitution patterns at the C-5 position of the oxazolidinone ring have been shown to significantly affect both antibacterial activity and MAO inhibition to varying degrees. Also, the antibacterial activity of compounds containing iron-chelating functionalities, such as the hydroxamic acids, 8-hydroxyquinolines and catechols have been correlated to their ability to alter iron intake and/or metabolism. Hence a series of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives were synthesized and evaluated for their antibacterial and MAO-A and -B inhibitory activities. The compounds were devoid of significant antibacterial activity but most demonstrated moderate MAO-A and -B inhibitory activities. Computer modeling studies revealed that the lack of potent antibacterial activity was due to significant steric interaction between the hydroxamic acid N-OH oxygen atom and one of the G2540 5′-phosphate oxygen atoms at the bacterial ribosomal binding site. Therefore, the replacement of the 5-acetamidomethyl group of linezolid with the 5-(N-hydroxyacetamido)methyl group present in the hydroxamic acid oxazolidinone derivatives was concluded to be detrimental to antibacterial activity. Furthermore, the 5-(hydroxamic acid)methyl oxazolidinone derivatives were also less active as MAO-A and -B inhibitors compared with linezolid and the selective inhibitors clorgyline and pargyline. In general, the 5-(hydroxamic acid)methyl oxazolidinone derivatives demonstrated moderate but selective MAO-B inhibitory activity.

PROCESS FOR THE PREPARATION OF STABLE CRYSTALLINE FORM-I OF LINEZOLID, SUBSTANTIALLY FREE OF RESIDUAL SOLVENT

-

Paragraph 0131; 0132, (2015/02/18)

The invention relates to a substantially pure linezolid hydroxide having R-isomer content more than about 99.9% relative to its S-isomer. Further aspect of invention provides the ambient moisture condition, which is critical for enantiomeric pure linezolid hydroxide. The obtained substantially enantiomerically pure linezolid hydroxide compound of formula-II can be subsequently converted into the linezolid compound of formula-I, having S-isomer content more than 99.9% relative to R-isomer. Further the invention provides an improved process for preparation of enantiomeric pure linezolid Form-I, wherein linezolid Form-I having the purity more than 99.9% relative to any other known polymorphic form of linezolid. The obtained enantiomeric pure linezolid Form-I can be subsequently converted into the other known polymorphic forms linezolid. The invention also provides stable and substantially solvent-free crystal of Form-I of linezolid.

PROCESS FOR PREPARATION OF CRYSTALLINE FORM I OF LINEZOLID AND ITS COMPOSITIONS

-

Page/Page column 14, (2015/05/26)

The present invention relates to a process for the preparation of crystalline form I of linezolid, comprising providing a solution of linezolid in a solvent, crystallizing and recovering the solid of Linezolid in crystalline form I at elevated temperature. The present invention also relates to the use of crystalline form I of linezolid prepared by the method of the present invention for preparing pharmaceutical compositions.

Convenient synthesis of the antibiotic linezolid via an oxazolidine-2,4-dione intermediate derived from the chiral building block isoserine

Greco, Arianna,De Marco, Rossella,Tani, Sara,Giacomini, Daria,Galletti, Paola,Tolomelli, Alessandra,Juaristi, Eusebio,Gentilucci, Luca

, p. 7614 - 7620 (2015/04/22)

We describe a new synthesis of the 5-(aminomethyl)oxazolidin-3-one core of linezolid in enantiomerically pure form. The expedient cyclization of the α-hydroxy amide derived from isoserine and 3-fluoro-4-morpholinoaniline to give the corresponding (aminomethyl)oxazolidine-2,4-dione, followed by its mild selective reduction at the C(4)-position, gave linezolid in almost quantitative overall yield. The 1,3-oxazolidin-2-one core of linezolid was obtained from isoserine in just three steps and with almost quantitative overall yield; the key features of the protocol are the expedient formation of the intermediate oxazolidine-2,4-dione, and its regioselective reduction at the 4-position.

PROCESS FOR THE PREPARATION OF CRYSTALLINE LINEZOLID

-

, (2013/06/05)

The present invention discloses a stable crystalline Form-I of linesolid process for preparation thereof.

Novel promising linezolid analogues: Rational design, synthesis and biological evaluation

De Rosa, Margherita,Zanfardino, Anna,Notomista, Eugenio,Wichelhaus, Thomas A.,Saturnino, Carmela,Varcamonti, Mario,Soriente, Annunziata

, p. 779 - 785 (2013/10/22)

A new series of 5-substituted oxazolidinones derived from linezolid, having urea and thiourea moieties at the C-5 side chain of the oxazolidinone ring, were prepared and their in vitro antibacterial activity was evaluated. The compound 10f demonstrated high antimicrobial activity, comparable to that of linezolid against Staphylococcus aureus.

NOVEL PROCESS FOR PREPARATION OF LINEZOLID AND ITS NOVEL INTERMEDIATES

-

, (2014/01/07)

A novel process for preparing oxazolidinone antibacterial agent Linezolid including key intermediates of oxazolidinones comprising: reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin; carbonylation to form oxazolidinone derivative; acetylation of (5R)-5-(chloromethyl)-3-(3-fluoro-4-morpholinophenyl-oxazolidin-2-one with sodium acetate to get novel intermediate; hydrolysis of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl acetate; mesylation of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol; reaction of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl methane sulphonate with potassium phthalimide; hydrolysis of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl phthalimide with hydrazine hydrate; acetylation of (S)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl amine with acetic anhydride yields Linezolid in high yield.

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