Pyridine → N-(3-Formamido-2-oxoazetidin-3-yl)-2-phenoxyacetamide

HRID 2118554Notes

Reaction equation

HRID 2118554 reaction equation
[NH2:1][C:2]1([NH:7][C:8](=[O:17])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][NH:4][C:3]1=[O:6].N1C=CC=CC=1.[C:24](OC=O)(=[O:26])C>ClCCl>[CH:24]([NH:1][C:2]1([NH:7][C:8](=[O:17])[CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:5][NH:4][C:3]1=[O:6])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 75269Acetic-formic anhydrideHCID 20193893N-(3-Amino-2-oxoazetidin-3-yl)-2-phenoxyacetamide

Product 1

HCID 20162888N-(3-Formamido-2-oxoazetidin-3-yl)-2-phenoxyacetamideYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The amine (27) (66 mg) in dry dichloromethane (5 ml) was cooled to 0° and treated with pyridine (49 mg) followed by formic-acetic anhydride (27 mg). The mixture was stirred at 0° for 15 minutes then allowed to warm to room temperature over 15 minutes, and evaporated to dryness. The residue was chromatographed on silica gel to give the product (28) (53 mg).

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-4432247a9a624c7b939ff6668434f4c0
Source dataset
uspto-grants-1987_07
Patent number
US04678782

Reaction notes

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