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

HRID 1905654Notes

Reaction equation

HRID 1905654 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-1f2a519fad954e04a0cd2989fc84efa0
Source dataset
uspto-grants-1987_03
Patent number
US04647558

Reaction notes

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