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

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 152305-23-2 differently. You can refer to the following data:
1. Zolmitriptan intermediate
2. (S)-4-(4-Aminobenzyl)-2-(1H)-oxazolidinone is an intermediate of zolmitriptan (sc-220415) which acts as a novel inhibitor of the cytochrome P-450 enzyme aromatase.
3. An intermediate of Zolmitriptan, as a novel inhibitor of the cytochrome P-450 enzyme aromatase

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

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

Downstream Products

• 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.

Design, synthesis, and evaluation of 4-(4′-aminobenzyl)-2-oxazolidinones as novel inhibitors of the cytochrome P-450 enzyme aromatase

The synthesis of a series of N-alkylated 4-(4′aminobenzyl)-2-oxazolidinones is described using a synthetically useful scheme which avoids the use of phosgene - since the derivatization is undertaken with the oxazolidin-2-one ring intact. The compounds were tested for human placental aromatase (AR) inhibition in vitro, using [1β, 2β-3H]androstenedione as substrate for the AR enzyme. The compounds were found, in general, to be more potent than the standard compound, amino-glutethimide (AG), and as such proved to be good lead compounds in the search for more specific AR inhibitors.

One pot synthesis of 2-oxazolidinone derivatives

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