Acetic-formic anhydride → HCID 86738871, compound

HRID 851386Notes

Reaction equation

HRID 851386 reaction equation
[NH2:1][C@H:2]1[C:5](=[O:6])[NH:4][C@@H:3]1[CH2:7][C:8]([O:14][CH3:15])=[CH:9][C:10]([O:12][CH3:13])=[O:11].[CH:16](OC(=O)C)=[O:17]>>[CH:16]([NH:1][C@H:2]1[C:5](=[O:6])[NH:4][C@@H:3]1[CH2:7][C:8]([O:14][CH3:15])=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[O:17]

Participants

3

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 70517408HCID 70517408, compound

Product 1

HCID 86738871HCID 86738871, compound

Procedure

A solution of methyl 4-[(2R,3R)-3-amino-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (145 mg) in acetic formic anhydride (1 ml) was stirred at 5° C. for one hour. The resultant solution was evaporated in vacuo, and the residue was chromatographed on silica gel (2.5 g) eluting with 3 to 5% methanol in dichloromethane to give methyl 4-[(2R,3R)-3-formamido-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (133 mg) as an amorphous solid.

Workup

  1. customThe resultant solution was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel (2.5 g)
  3. washeluting with 3 to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-cd1ccd54756a42c58cd57bf2a5e32b61
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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