152305-23-2

Basic information

• Product Name: (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone
• Synonyms: (4S)-4-[(4-AMINOPHENYL)METHYL]-2-OXAZOLIDINONE;(S)-4-(4'-AMINOBENZYL)-1,3-OXAZOLIDIN-2-ONE;(S)-4-(4-AMINOBENZYL)-1,3-OXAZOLIDIN-2-ONE;(S)-4-(4-AMINOBENZYL)-2(1H)-OXAZOLIDINONE;(S)-4-(4'-AMINOBENZYL)-2-OXAZOLIDINONE;(S)-4-(4-AMINOBENZYL)-2-OXAZOLIDINONE;(S)-4-(4-AMINO-BENZYL)-OXAZOLIDIN-2-ONE;(S)-4-(4-AMINO-BENZYL)-OXAZOLIDINE-2-ONE
• CAS NO: 152305-23-2
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21
• Product Categories: INTERMEDIATESOFZOLMITRIPTAN;chiral;Chiral Reagents;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Intermediates & Fine Chemicals;Pharmaceuticals;API's
• Mol File: 152305-23-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 107-111 °C
• Boiling Point: 479.7 °C at 760 mmHg
• Flash Point: 243.9 °C
• Appearance: white crystalline powder
• Density: 1.257 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -6.0 ° (C=1, MeOH)
• Storage Temp.: Room temperature.
• Solubility: Soluble in dimethyl sulfoxide and methanol.
• PKA: 12.67±0.40(Predicted)
• CAS DataBase Reference: (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone(152305-23-2)
• EPA Substance Registry System: (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone(152305-23-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 2
• Hazardous Substances Data: 152305-23-2(Hazardous Substances Data)

Usage

Description

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is a white to light yellow crystalline powder with unique chemical properties that make it a valuable component in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone is used as an intermediate for the synthesis of zolmitriptan (sc-220415), which is a novel inhibitor of the cytochrome P-450 enzyme aromatase. This application is significant because it helps in the development of new treatments for various medical conditions.
Used in Aromatase Inhibition:
(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone is used as an intermediate in the creation of zolmitriptan, a compound that acts as a novel inhibitor of the cytochrome P-450 enzyme aromatase. This inhibition is crucial in the treatment of certain hormonally driven conditions, such as breast cancer, by reducing the production of estrogen in the body.
Used in Drug Synthesis:
(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it an essential building block in the development of new drugs, contributing to the advancement of medical treatments and therapies.

InChI:InChI=1/C10H12N2O2/c11-8-3-1-7(2-4-8)5-9-6-14-10(13)12-9/h1-4,9H,5-6,11H2,(H,12,13)

Synthetic route

(S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one (139264-55-4) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 760 Torr; Ambient temperature;	79%
With indium; ammonium chloride In ethanol for 4h; Heating;	47%
With hydrogen; nickel In methanol at 30℃; for 6 - 7h;

(S)-2-amino-3-(4-aminophenyl)propan-1-ol (726134-79-8) + Diethyl carbonate (105-58-8) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
potassium carbonate at 115 - 135℃; for 2.5h;	75%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + MeX → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / fuming HNO3 / CH2Cl2 / 2 h / 20 °C 2: 47 percent / NH4Cl; In / ethanol / 4 h / Heating View Scheme

L-phenylalanine (63-91-2) + PhMgHal → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 53 percent / conc. H2SO4, conc. HNO3 / 0.5 h / Ambient temperature 2: 76 percent / SOCl2 / 4 h / -10 - 40 °C 3: 65 percent / NaBH4 / ethanol; H2O / 4 h / Heating 4: 75 percent / 0.2M aq. KOH / toluene / 2 h / 0 - 20 °C 5: 79 percent / H2, aq. HCl / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

4-nitro-3-phenyl-L-alanine (949-99-5) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 76 percent / SOCl2 / 4 h / -10 - 40 °C 2: 65 percent / NaBH4 / ethanol; H2O / 4 h / Heating 3: 75 percent / 0.2M aq. KOH / toluene / 2 h / 0 - 20 °C 4: 79 percent / H2, aq. HCl / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

(S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol (89288-22-2) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / 0.2M aq. KOH / toluene / 2 h / 0 - 20 °C 2: 79 percent / H2, aq. HCl / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

(S)-4-nitrophenylalanine methyl ester hydrochloride (17193-40-7) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / NaBH4 / ethanol; H2O / 4 h / Heating 2: 75 percent / 0.2M aq. KOH / toluene / 2 h / 0 - 20 °C 3: 79 percent / H2, aq. HCl / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

(S)-N-butoxycarbonyl-4-aminophenylalaninol (188404-34-4) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2)

Conditions	Yield
With sodium methylate In methanol; butan-1-ol at 5 - 85℃; for 8.5h;

4-iodophenyl isothiocyanate (2059-76-9) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-iodophenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	90%

1-isothiocyanato-4-methylbenzene (622-59-3) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-3-p-tolylthiourea

Conditions	Yield
With triethylamine In acetone Reflux;	88%

p-nitrophenyl isothiocyanate (2131-61-5) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-nitrophenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)-phenyl)thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	82%

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) + 4-Bromophenyl isothiocyanate (1985-12-2) → (S)-1-(4-bromophenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)-phenyl)thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	80%

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) + 4-bromobenzenesulfonyl chloride (98-58-8) → (S)-4-bromo-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	79%

ethyl 2-acetyl-5-(1,3-dioxo-1,3-dihydro-2-isoindolyl)pentanoate (55747-45-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → ethyl (S)-3-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate (868622-21-3)

Conditions	Yield
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In methanol; water at -5 - 0℃; Industrial scale; Stage #2: ethyl 2-acetyl-5-(1,3-dioxo-1,3-dihydro-2-isoindolyl)pentanoate With sodium acetate In methanol; water at 0 - 30℃; Industrial scale; Stage #3: With hydrogenchloride In methanol for 6h; Fischer Indole Synthesis; Reflux; Industrial scale;	78%

benzaldehyde (100-52-7) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-((E)-4-(benzylideneamino)benzyl)oxazolidin-2-one

Conditions	Yield
In methanol at 20℃; for 0.0833333h;	77.5%

p-toluenesulfonyl chloride (98-59-9) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-methyl-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	76%

4-chloro-benzoyl chloride (122-01-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-chloro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	75%

benzenesulfonyl chloride (98-09-9) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	72%

4-nitro-benzoyl chloride (122-04-3) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-nitro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	58%

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-methoxy-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	57%

4-methoxy-benzoyl chloride (100-07-2) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-methoxy-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	54%

4-Fluorobenzenesulfonyl chloride (349-88-2) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-fluoro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	53%

4-fluorobenzoyl chloride (403-43-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-fluoro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	50%

4-chlorobenzoyl chloride (586-75-4) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-bromo-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	48%

benzoyl chloride (98-88-4) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	47%

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-(3-iodo-4-aminobenzyl)-1,3-oxazolidin-2-one (179534-87-3)

Conditions	Yield
With Iodine monochloride; calcium carbonate In methanol; ethyl acetate	45%
With Iodine monochloride; calcium carbonate In methanol for 16h; Ambient temperature;

4-fluorophenyl isothiocyanate (1544-68-9) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-fluorophenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)-phenyl)thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	42%

phenyl isothiocyanate (103-72-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-3-phenylthiourea

Conditions	Yield
With triethylamine In acetone Reflux;	33%

4-chlorobenzenesulfonyl chloride (98-60-2) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-chloro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	31%

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → (S)-4-nitro-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	28%

4-Methoxyphenyl isothiocyanate (2284-20-0) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-methoxyphenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)-phenyl)thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	27%

4-methyl-benzoyl chloride (874-60-2) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-4-methyl-N-(4-((2-oxooxazolidin-4-yl)methyl)phenyl)-benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	24%

4-Chlorophenyl isothiocyanate (2131-55-7) + (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-1-(4-chlorophenyl)-3-(4-((2-oxooxazolidin-4-yl)methyl)-phenyl)thiourea

Conditions	Yield
With triethylamine In acetone Reflux;	19%

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → 4-((S)-2-Oxo-oxazolidin-4-ylmethyl)-benzenediazonium; chloride

Conditions	Yield
With hydrogenchloride; sodium nitrite at 0℃; for 0.5h;
With hydrogenchloride; sodium nitrite In water at -10 - 30℃; for 3h;
With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2) → (S)-2-<5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl>ethyl alcohol (179636-99-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: ICl, CaCO3 / methanol / 16 h / Ambient temperature 2: Na2CO3, MgSO4, Pd(OAc)2 / dimethylformamide / 16 h / 110 °C 3: 5 N HCl / methanol / 19 h / Ambient temperature View Scheme

Upstream product

• 139264-55-4 (S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 63-91-2 L-phenylalanine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 89288-22-2 (S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol 
• 17193-40-7 (S)-4-nitrophenylalanine methyl ester hydrochloride 
• 188404-34-4 (S)-N-butoxycarbonyl-4-aminophenylalaninol 
• 726134-79-8 (S)-2-amino-3-(4-aminophenyl)propan-1-ol 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 191864-24-1 ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate 
• 187975-62-8 (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one 
• 139264-17-8 zolmitriptan 
• 139264-57-6 (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN

Disclosed herein the process for producing pure" Zolmitriptan employing improved reaction conditions which excluded the use of column chromatography.

A process for the purification of (S)-4-((3-(dimethylamino)ethyl)-1H-indol-5yl)-methyl)-2-oxazolidinone

A process for the purification of (S)-4-{[3-(dimethylamino)ethyl]-1H-indol-5yl]-methyl}-2-oxazolidinone and non-solvated, pure (S)-4-{[3-(dimethylamino) ethyl]-1H-indol-5y1]-methyl}-2-oxazolidinone.

One pot synthesis of 2-oxazolidinone derivatives

The invention provides an improved process for preparing compounds of formula (I)