(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

Base Information

• Chemical Name: (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone
• CAS No.: 152305-23-2
• Molecular Formula: C10H12N2O2
• Molecular Weight: 192.217
• Hs Code.: 29349990
• UNII: BJO4G2UWA4
• DSSTox Substance ID: DTXSID301285890
• Nikkaji Number: J694.105B
• Mol file: 152305-23-2.mol

Synonyms:2-Oxazolidinone,4-[(4-aminophenyl)methyl]-, (S)-;(4S)-4-(4-Aminobenzyl)-1,3-oxazolidin-2-one;(S)-4-(4-Aminobenzyl)-2-oxazolidinone;

Chemical Property of (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 107-111 °C
• Refractive Index: -6.0 ° (C=1, MeOH)
• Boiling Point: 479.7 °C at 760 mmHg
• PKA: 12.67±0.40(Predicted)
• Flash Point: 243.9 °C
• PSA: 64.35000
• Density: 1.257 g/cm³
• LogP: 1.82970
• Storage Temp.: Room temperature.
• Solubility.: Soluble in dimethyl sulfoxide and methanol.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 192.089877630
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-(4-Aminobenzyl)-2-(1H)-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)CC2=CC=C(C=C2)N
• Isomeric SMILES: C1[C@@H](NC(=O)O1)CC2=CC=C(C=C2)N
• Uses: Zolmitriptan intermediate (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. An intermediate of Zolmitriptan, as a novel inhibitor of the cytochrome P-450 enzyme aromatase

Technology Process of (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

There total 9 articles about (S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one (139264-55-4) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2,262857-90-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr; Ambient temperature;

DOI:10.1021/jm9605849

Reference yield: 75.0%

(S)-2-amino-3-(4-aminophenyl)propan-1-ol (726134-79-8) + Diethyl carbonate (105-58-8,76619-83-5) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2,262857-90-9)

Guidance literature:

potassium carbonate; at 115 - 135 ℃; for 2.5h;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one (152305-23-2,262857-90-9)

Guidance literature:

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

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal; In ethanol; water; toluene;

DOI:10.1021/jm9605849

upstream raw materials:

(S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one

(S)-4-Benzyl-2-oxazolidinone

L-phenylalanine

4-nitro-3-phenyl-L-alanine

Downstream raw materials:

ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one

zolmitriptan

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride

Refernces

• 1、 -. "A NOVEL AND AN IMPROVED PROCESS FOR THE PREPARATION OF (S)-4-(4-AMINOBENZYL)-2- OXAZOLIDINONE". Page 9; 12; 14; 16-18. . Retrieved 2008/06/13.
• 2、 -. "A process for the purification of (S)-4-((3-(dimethylamino)ethyl)-1H-indol-5yl)-methyl)-2-oxazolidinone". Example 1. . Retrieved 2010/01/31.