3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-

Base Information

• Chemical Name: 3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-
• CAS No.: 198021-41-9
• Molecular Formula: C17H14ClNO3
• Molecular Weight: 315.756
• DSSTox Substance ID: DTXSID50448993
• Nikkaji Number: J1.024.143J
• Wikidata: Q82268252
• Mol file: 198021-41-9.mol

Synonyms:3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-;198021-41-9;SCHEMBL9600224;DTXSID50448993;ONCPUTDNWCACRL-JKSUJKDBSA-N;(4,5-cis-Diphenyl-2-oxo-3-oxazolidinyl)acetyl chloride;(4S)-2-Oxo-4beta,5beta-diphenyloxazolidine-3-acetic acid chloride

Chemical Property of 3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 315.0662210
• Heavy Atom Count: 22
• Complexity: 416

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(OC(=O)N2CC(=O)Cl)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]2[C@H](OC(=O)N2CC(=O)Cl)C3=CC=CC=C3

Technology Process of 3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-

There total 3 articles about 3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)- 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: 98.0%

[(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]acetic acid (198021-38-4) → [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride (198021-41-9)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1002/chem.19970030909

Reference yield:

((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-acetic acid methyl ester → [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride (198021-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / tetrahydrofuran / 2 h / Ambient temperature

2: 98 percent / (COCl)2, DMF / CH₂Cl₂ / 1 h / Ambient temperature

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.19970030909

Reference yield:

ethyl [(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]acetate (1147849-07-7) → [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride (198021-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / tetrahydrofuran / 20 °C

2: oxalyl dichloride / toluene / 2.5 h

With oxalyl dichloride; water; sodium hydroxide; In tetrahydrofuran; toluene;

DOI:10.1016/j.tetlet.2014.11.041

upstream raw materials:

[(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]acetic acid

ethyl [(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]acetate

Downstream raw materials:

(3S,4R)-1-[bis(trimethylsilyl)methyl]-4-phenyl-3-[(4S,5R)-4,5-diphenyl-2-oxo-oxazolidin-3-yl]-azetidin-2-one

tert-butyl-2-((3S,4R)-2-oxo-3-((4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl)-4-((E)-styryl)azetidin-1-yl)acetate