Dimethylformamide → HCID 10890011, compound

HRID 553413Notes

Reaction equation

HRID 553413 reaction equation
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:20])=O.CN(C)C=O>ClCCl>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([Cl:20])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 853681(S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid

Product 1

HCID 10890011HCID 10890011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 equivalent of (4(S)-phenyloxazolidin-2-on-3-yl)acetic acid (Evans, U.S. Pat. No. 4,665,171) and 1.3 equivalent of oxalyl chloride in 200 mL dichloromethane was treated with a catalytic amount of anhydrous dimethylformamide (85 μL/milliequivalent of acetic acid derivative) resulting in vigorous gas evolution. After 45 minutes all gas evolution had ceased and the reaction mixture was concentrated under reduced pressure to provide the title compound as an off-white solid after drying for 2 h under vacuum.

Workup

  1. customresulting in vigorous gas evolution
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cbf28d41e1143919c8fbdf7395a26de
Source dataset
uspto-grants-2011_11
Patent number
US08048874B2

Reaction notes

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