Dimethylformamide → HCID 10890011, compound

HRID 397307Notes

Reaction equation

HRID 397307 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

To a solution of 1.31 gm (5.93 mMol) (4(S)-phenyloxazolidin-2-on-3-yl)acetic acid (Evans, U.S. Pat. No. 4,665,171) in 200 mL dichloromethane was added 0.67 mL (7.71 mMol) oxalyl chloride. To this solution was then added 0.5 mL anhydrous dimethylformamide which resulted in vigorous gas evolution. After 45 minutes all gas evolution had ceased and the reaction mixture was concentrated under reduced pressure. The title compound, recovered as an off-white solid, was dried at 0.5 mm Hg for 10 minutes before use in subsequent reactions.

Workup

  1. customresulted in vigorous gas evolution
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe title compound, recovered as an off-white solid
  4. customwas dried at 0.5 mm Hg for 10 minutes before use in subsequent reactions

Sources & evidence

ORD record
ord-f02aee7a15734e478d2658750dc3c68c
Source dataset
uspto-grants-2003_08
Patent number
US06610680B1

Reaction notes

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