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90719-32-7

Basic Information
CAS No.: 90719-32-7
Name: (S)-4-Benzyl-2-oxazolidinone
Molecular Structure:
Molecular Structure of 90719-32-7 ((S)-4-Benzyl-2-oxazolidinone)
Formula: C10H11NO2
Molecular Weight: 177.20
Synonyms: (4S)-4-benzyloxazolidin-2-one;S-4-benzyl-2-oxazolidinone;(S)-4-Benzyl-4-oxazolidinone;(S)-4-benzyl-2-oxazolidone;(S)-(-)-4-Benzyl-2-oxazolidincne;(S)-4-Benzyl-2-0xazolidinone;(S)-4-Benzyloxazolidin-2-one;(S)-(-)-4-benzyl-2-oxazolidinone;(S)-4-Benzyl-oxazolidin-2-one;S-(+)-4-Benzyl-2-oxazolidinone;S-4-Bhenyl-2-Oxazolidinone;(4S)-4-Benzyl-1,3-oxazolidin-2-one;(S)-4-(Benzyl)-2-Oxazolidinone;(S)-(+)-4-Benzyl-2-Oxazolidinone;(S)-4-benzyl-2-oxazolidenone;
EINECS: 618-632-6
Density: 1.176 g/cm3
Melting Point: 86-88 °C(lit.)
Boiling Point: 398.8 °C at 760 mmHg
Flash Point: 195 °C
Solubility: Insoluble in water.
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information:
PSA: 38.33000
LogP: 1.66630
Synthetic route
3182-95-4

L-Phenylalaninol

105-58-8

Diethyl carbonate

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 120 - 130℃; for 3h;100%
With potassium carbonate In ethanol at 130 - 135℃; for 1h;88%
With potassium carbonate at 135 - 140℃; for 2h;84%
717137-43-4

(4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one

A

614-19-7, 3646-50-2, 13921-90-9, 40856-44-8

(R)-3-phenyl-3-aminopropionic acid

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h;
Stage #2: With hydrogenchloride In water pH=1 - 2;
Stage #3: With Pearlman's catalist; hydrogen In methanol at 20℃; for 24h;
A 43%
B 100%
213385-64-9

(S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one

A

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

B

221292-86-0

(2S,4S)-2-Azido-4-methyl-hexanoic acid

Conditions
ConditionsYield
Stage #1: (S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h;
Stage #2: With hydrogenchloride In water pH=1 - 2;
A 99%
B 96.7%
67-56-1

methanol

181431-20-9

(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone

A

29393-16-6

methyl (2R)-2-methyl-3-phenylpropanoate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃; for 72h;A 98%
B 99%
64-17-5

ethanol

198649-20-6

(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

A

106-33-2

ethyl laurate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;A 99%
B 99%
198649-20-6

(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

100-51-6

benzyl alcohol

A

140-25-0

benzyl dodecanoate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;A 83%
B 99%
131685-53-5, 101711-78-8

(S)-4-benzyl-3-propionyl-2-oxazolidinone

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With methanol; C17H23BN2O at 25℃; under 760.051 Torr; for 1h; Inert atmosphere; chemoselective reaction;98%
Multi-step reaction with 2 steps
1: 1.) di-n-butylboron triflate, N,N-diisopropylethylamine, 3.) aq. H2O2 / 1) CH2Cl2, 0 deg C, 30 min; 2) CH2Cl2, -78 deg C, 45 min, 0 deg C, 2 h; 3) methanol, 0 deg C, 1 h
2: 1.) trimethylaluminum / 1) CH2Cl2, toluene, rt, 1 h; 2) CH2Cl2, toluene, -20 deg C --> rt, rt, 1.5 h
View Scheme
Multi-step reaction with 2 steps
1: 1.) dibutylboron trifluoromethanesulfonate, diisopropylethylamine / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, -78 deg C (1 h), room temp. (5 h)
2: 80 percent / LiBH4, H2O / tetrahydrofuran / 3 h / Ambient temperature
View Scheme

(S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (1'R,2'S,7a'R,11R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 98%
B 96%
373363-70-3

N-(4-benzyl-2-oxo-oxazolidin-3-yl)-N-(5-chloro-1-propyl-pentyl)-benzamide

A

373363-71-4

N-(5-chloro-1-propyl-pentyl)-benzamide

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.166667h;A 97%
B n/a
1352791-77-5

tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate

A

1352791-75-3

(3R)-2-[3-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water for 3h;A 97%
B 89%

(S)-4-benzyl-3-((1'S,2'S,3'R,7a'R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (1'S,2'S,7a'R,11R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 97%
B n/a

(S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-7,8-dimethyl-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (1'R,2'S,7a'R,11R)-7,8-dimethyl-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 97%
B n/a
181431-20-9

(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone

A

14367-67-0

2-methyl-3-phenylpropionic acid

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone With ytterbium(III) triflate In methanol for 3h;
Stage #2: With lithium hydroxide In tetrahydrofuran; water for 2h;
A 97%
B 97%
161646-29-3

(S)-ethyl (1-hydroxy-3-phenylpropan-2-yl)carbamate

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With potassium carbonate In toluene for 3h; Heating;96%
With potassium carbonate at 100 - 130℃;
With hydrotalcite; magnesium aluminum In toluene at 110℃; for 5h;91 % Spectr.
With potassium carbonate at 125 - 130℃; under 33.7534 - 37.5038 Torr;
With polyethylene glycol 400(PEG-400) In toluene Reflux; Large scale;167 kg
138649-96-4

(4S)-3-<(2S,3S)-3-hydroxy-2-methyl-1-oxo-3-(1-phenylsulfanylcyclopentyl)propyl>-4-phenylmethyl-1,3-oxazolidin-2-one

A

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

B

138751-07-2

(1S,2S)-2-methyl-1-(1-phenylsulfanylcyclopentyl)propane-1,3-diol

Conditions
ConditionsYield
With lithium borohydride; water In tetrahydrofuran for 3h; Ambient temperature;A 80%
B 96%
201230-82-2

carbon monoxide

3182-95-4

L-Phenylalaninol

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium acetate; palladium diacetate In acetonitrile at 20℃; under 760 Torr; Electrolysis;96%
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating;88%
With oxygen; copper-(N-heterocyclic carbene) complex In 1,4-dioxane at 100℃; under 37503.8 Torr; for 3h;86%
19213-72-0

ethyl 1-imidazolecarboxylate

3182-95-4

L-Phenylalaninol

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 15h; Reflux;96%

(S)-4-benzyl-3-((2'R,3'S,4'R)-1'-methyl-4'-phenylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (3'S,4'R,11R)-1'-methyl-4'-phenylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 96%
B n/a

(S)-4-benzyl-3-(4-methoxyphenyl)oxazolidin-2-one

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.0833333h;95%

(S)-4-benzyl-3-((1'S,2'S,3'R,7a'R)-1',7,8-trimethyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (1'S,2'S,7a'R,11R)-1',7,8-trimethyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 95%
B n/a

(S)-4-benzyl-3-[(E)-2-(phenylsulfonyl)ethenyl]-1,3-oxazolidin-2-one

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With pyrrolidine In acetonitrile at 55℃; for 4.5h; Inert atmosphere;94%

(S)-4-benzyl-3-((2'R,3'S,4'S)-1',4'-dimethylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-ylcarbonyl)oxazolidin-2-one

616-38-6

carbonic acid dimethyl ester

A

methyl (3'S,4'S,11R)-1',4'-dimethylspiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidine]-3'-carboxylate

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium methylate In dichloromethane at 20℃; for 4h;A 92%
B n/a
622-33-3

N-benzyloxyamine

153729-83-0

(S)-3-benzoyl-4-phenylmethyl-2-oxazolidinone

A

3532-25-0

N-benzyloxy benzamide

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With samarium(III) trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.5h;A 91%
B n/a
67-56-1

methanol

(4S)-3-((3S,2R)-3-hydroxy-2-methyl-3-phenylpropanoyl)-4-benzyl-1,3-oxazolidin-2-one

A

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

B

36041-80-2

(2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate

Conditions
ConditionsYield
With C17H23BN2O at 25℃; under 760.051 Torr; for 48h; Inert atmosphere; chemoselective reaction;A 91%
B 89%
131744-19-9, 145588-94-9

(4S)-4-benzyl-1,3-oxazolidine-2-thione

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With methyloxirane In chloroform at 150℃; for 1h; Inert atmosphere; Microwave irradiation;90%
With sodium hydroxide; dihydrogen peroxide In water Ambient temperature;56%
3182-95-4

L-Phenylalaninol

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
In N,N-dimethyl acetamide for 0.0333333h; Cyclization; microwave heating;90%
124-38-9

carbon dioxide

3182-95-4

L-Phenylalaninol

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With caesium carbonate In dimethylsulfoxide-d6 at 25 - 150℃; under 2280.15 Torr; for 24h; Schlenk technique; Autoclave;90%
Stage #1: carbon dioxide; L-Phenylalaninol With N(Et)4(1+)*(2-pyrrolidone-anion) In acetonitrile at 20℃; for 1h; Carboxylation;
Stage #2: With p-toluenesulfonyl chloride In acetonitrile at 20℃; Cyclization; Further stages.;
71%
With Hexamethylcyclotrisiloxane; tetrabutyl ammonium fluoride In dimethylsulfoxide-d6 at 150℃; under 760.051 Torr; for 9h; Reagent/catalyst; chemoselective reaction;78 %Spectr.
3182-95-4

L-Phenylalaninol

81420-42-0

mononitrophenyl carbonate

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With dmap In dichloromethane for 3h;90%
1441063-84-8

(S,E)-4-benzyl-3-(3-oxobut-1-en-1-yl)oxazolidin-2-one

112-55-0

1-dodecylthiol

A

C16H30OS

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 0.3h; Inert atmosphere;A n/a
B 90%

(3R)-3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]hexanenitrile

A

(R)-3-(hydroxymethyl)hexanenitrile

B

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 2h;A 89.2%
B 1.05 g
With sodium tetrahydroborate; water In tetrahydrofuran at 20 - 40℃; for 2h;A 89.2%
B 1.05 g
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

79-03-8

propionyl chloride

131685-53-5, 101711-78-8

(S)-4-benzyl-3-propionyl-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In tetrahydrofuran at 0℃; for 1.16667h;
Stage #2: propionyl chloride In tetrahydrofuran at 0 - 20℃;
100%
With n-butyllithium In tetrahydrofuran100%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;99%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

802294-64-0

propionic acid

131685-53-5, 101711-78-8

(S)-4-benzyl-3-propionyl-2-oxazolidinone

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;100%
With 2-chloro-1-methylpyridinium p-toluenesulfonate; triethylamine In dichloromethane at 20℃; for 7h;94.4%
With triethylamine In tetrahydrofuran80%
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran
With 4-methyl-morpholine; chloroformic acid ethyl ester; lithium chloride In tetrahydrofuran
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

108-12-3

isopentanoyl chloride

145589-03-3, 104266-90-2

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium; triphenylmethane In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: isopentanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h;
Stage #3: With potassium carbonate In tetrahydrofuran; hexane; water
100%
With triethylamine; dmap In dichloromethane at 0 - 10℃; for 0.5h;95%
With dmap In dichloromethane; water at 0 - 10℃; for 0.5h;95%
24424-99-5

di-tert-butyl dicarbonate

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

132836-68-1

(S)-3-(tert-butoxycarbonyl)-4-benzyl-2-oxazolidinone

Conditions
ConditionsYield
With dmap In acetonitrile at 25℃; for 0.116667h;100%
39716-58-0

pent-4-enoyl chloride

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

104266-88-8

(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With n-butyllithium100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: pent-4-enoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
99%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;97%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

196491-68-6

3-[dimethyl(phenyl)silyl]glutaric anhydride

5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 24h;100%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane 1.) -35 deg C, 10 min, 2.) -78 deg C, 1 h;100%
With dmap In dichloromethane at 20℃;
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

598-21-0

2-Bromoacetyl bromide

129549-13-9

4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
With n-butyllithium at -78 - 20℃; for 0.5h;100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78 - 20℃; for 16.5h; Inert atmosphere;
92%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - -60℃; for 0.5h;
Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran; hexane at -78℃; for 1h;
87%
4224-70-8

6-bromohexanoic acid

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

203739-34-8

(S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 6-bromohexanoic acid In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
100%
With n-butyllithium; pivaloyl chloride; triethylamine Multistep reaction;
Stage #1: 6-bromohexanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -78 - 0℃;
Stage #2: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

299216-13-0

(S)-3-amino-4-benzyl-1,3-oxazolan-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With potassium hydride
Stage #2: With chloroamine In tert-butyl methyl ether
100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With sodium hydride In 1,4-dioxane; mineral oil at 60℃; for 1h;
Stage #2: In 1,4-dioxane; mineral oil at 20℃; for 6h;
86%
With n-butyllithium; O-(diphenylphosphinyl)hydroxylamine In tetrahydrofuran; hexane at 20℃; for 6h;80%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

621-82-9

Cinnamic acid

133812-18-7

(S)-4-benzyl-3-(6-(benzyloxy)hex-2-enoyl)oxazolidin-2-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;100%
104-97-2

cyclopentanepropanoyl chloride

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

(4S)-4-benzyl-3-(3-cyclopentylpropanoyl)-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
90%
927-58-2

4-bromobutyroyl chloride

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

1424402-18-5

(S)-4-benzyl-3-(4-bromobutanoyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromobutyroyl chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere;
100%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

109-52-4

valeric acid

143868-89-7

3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10 - 15℃; for 2h; Large scale;
Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride at 20℃; Large scale;
100%
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -20 - -15℃; for 1h; Inert atmosphere;
Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at -20 - 20℃; for 16h; Solvent; Temperature; Reagent/catalyst;
98.12%
Stage #1: valeric acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-4-Benzyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at 20 - 25℃; for 16h;
94%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

638-29-9

n-valeryl chloride

143868-89-7

3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -70 - -65℃; for 0.5h; Inert atmosphere;
Stage #2: n-valeryl chloride In tetrahydrofuran at -75 - -65℃; for 1h;
99.9%
With dmap; triethylamine In dichloromethane at 0 - 10℃; for 3h; Large scale;98%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: n-valeryl chloride In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
95%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

75-36-5

acetyl chloride

132836-66-9

(S)-3-acetyl-4-benzyloxazolidin-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at 0℃;99%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;94.5%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran Inert atmosphere;
Stage #2: acetyl chloride at -78℃; for 0.5h; Inert atmosphere;
82%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

141-75-3

butyryl chloride

111292-87-6, 143097-11-4, 112459-79-7

(S)-4-benzyl-3-butyryloxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: butyryl chloride In tetrahydrofuran at -78℃; for 3h;
99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: butyryl chloride In tetrahydrofuran at -78 - 20℃; for 2.25h;
98%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h;
Stage #2: butyryl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 3.67h;
98%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

318488-46-9

α-allyloxyacetyl pivaloyl anhydride

197721-28-1

(4S)-3-(2-allyloxyethanoyl)-4-benzyloxazolidin-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: α-allyloxyacetyl pivaloyl anhydride In tetrahydrofuran; hexane at -78 - 0℃; for 0.75h; Further stages.;
5.45 g
With n-butyllithium In tetrahydrofuran; diethyl ether at -78 - 0℃; for 0.75h;10.0 g
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

C11H18O4

197721-29-2

(S)-3-<1-oxo-2-(but-3-enyl-1-oxy)>-4-benzyl-2-oxazolidinone

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;99%
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction;
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

C12H20O4

197721-30-5

(S)-3-<1-oxo-2-(pent-4-enyl-1-oxy)>-4-benzyl-2-oxazolidinone

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;99%
With n-butyllithium 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min; Yield given; Multistep reaction;
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

122-78-1

phenylacetaldehyde

(4S)-4-benzyl-3-<(E)-2-phenylethenyl>-1,3-oxazolan-2-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene Reflux; Dean-Stark;99%
With 1,2,3-Benzotriazole; toluene-4-sulfonic acid In toluene for 48h; Heating;62%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

18496-54-3

phenylbutyric acid chloride

170450-77-8

(S)-4-benzyl-3-(3-phenylbutanoyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h;
99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: phenylbutyric acid chloride In tetrahydrofuran; n-heptane at -78 - 0℃; for 3.5h;
99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: phenylbutyric acid chloride In tetrahydrofuran at -78 - 0℃; for 3.5h;
99%
With n-butyllithium 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT; Yield given; Multistep reaction;
With n-butyllithium; triphenylmethane In tetrahydrofuran at -78℃;
623-03-0

4-Cyanochlorobenzene

90719-32-7

(S)-4-Benzyl-2-oxazolidinone

4-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]benzonitrile

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; johnphos In toluene at 115℃; for 15h;99%
With potassium phosphate; [(π-allyl)Pd(tBuBrettPhos)]OTf In tert-butyl alcohol at 110℃; for 3h; Schlenk technique; Inert atmosphere; Sealed tube;95%
With (PAd2-DalPhos)NiCl(o-tol); caesium carbonate In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;64%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

638-29-9

n-valeryl chloride

(R)-3-(1-valeroyl)-4-benzyloxazolidine-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; ethyl acetate99%
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

39098-75-4

3-cyclohexylpropionyl chloride

136187-43-4

(4S)-3-(3-cyclohexyl-1-oxopropyl)-4-phenylmethyl-2-oxazolidinone

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
99%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: 3-cyclohexylpropionyl chloride In tetrahydrofuran at -78 - 20℃;
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Chemistry

IUPAC Name: (4S)-4-benzyl-1,3-oxazolidin-2-one
Synonyms of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): (S)-(-)-4-Benzyl-2-oxazolidinone
CAS NO: 90719-32-7
Molecular formula: C10H11NO2
Molecular Weight: 177.2
Molecular Structure:
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.551
Molar Refractivity: 48.08 cm3
Molar Volume: 150.5 cm3
Surface Tension: 43.2 dyne/cm
Density: 1.176 g/cm3
Flash Point: 195 °C
Enthalpy of Vaporization: 64.95 kJ/mol
Boiling Point: 398.8 °C at 760 mmHg
Vapour Pressure: 1.43E-06 mmHg at 25°C
Melting point: 86-88 °C(lit.)
Alpha: -62 o (C=1, CHCl3)
Storage temp: 0-6°C
Sensitive: Hygroscopic
Appearance: white to light yellow crystal powder
Product Categories of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): Oxazolidinone;Chiral Compounds;chiral;Aromatics Compounds;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Aromatics;Chiral Reagents;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives

Uses

 (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7) is a kind  of  pharmaceutical intermediate.

Safety Profile

Safety Information about (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7):
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 3-10
HS Code: 29349990

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.