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90719-32-7

Basic Information
CAS No.: 90719-32-7
Name: (S)-4-Benzyl-2-oxazolidinone
Article Data: 183
Molecular Structure:
Molecular Structure of 90719-32-7 ((S)-4-Benzyl-2-oxazolidinone)
Formula: C10H11NO2
Molecular Weight: 177.203
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
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%
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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.