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

HRID 1762168Notes

Reaction equation

HRID 1762168 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([OH:22])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:26])=O>C1C=CC=CC=1>[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9](=[O:18])[N:8]2[CH2:19][C:20]([Cl:26])=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 58430307[(4S,5R)-2-Oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetic acid

Product 1

HCID 109359773-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-Yield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension composed of (4,5-cis-diphenyl-2-oxo-3-oxazolidinyl)acetic acid (29.1 g, 97.9 mmol), oxalyl chloride (18.6 g, 147 mmol) and benzene (120 ml) was refluxed for 2 hours. When the suspension became homogeneous, the solvent was distilled off. By the above procedure there was obtained the title compound (30.9 g) as light brown oil.

Workup

  1. temperaturewas refluxed for 2 hours
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-aa46dd4435d04b2cb110922d77ee3904
Source dataset
uspto-grants-1989_05
Patent number
US04831026

Reaction notes

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