Diazomethane → methyl [(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetate

HRID 851404Notes

Reaction equation

[N+](=[CH2:3])=[N-].[CH3:4][C:5]([C@H:21]1[C:24](=[O:25])[NH:23][C@@H:22]1[CH2:26][C:27]([OH:29])=[O:28])([O:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:9])[CH3:6]>CCOCC.C(Cl)Cl.CO.C(O)(=O)C>[CH3:6][C:5]([C@H:21]1[C:24](=[O:25])[NH:23][C@@H:22]1[CH2:26][C:27]([O:29][CH3:3])=[O:28])([O:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)=[O:9])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of diazomethane in ether (1 ml) was added to a solution of [(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]-acetic acid (29 mg) in a mixture of methylene chloride (1 ml) and methanol (1 ml) at 0° C. and the mixture was stirred for 15 minutes at 0° C. Acetic acid (1 drop) was added to the mixture at 0° C. and the mixture was evaporated in vacuo. The residue was chromatographed on silica gel (1 g) eluting with a mixture of methylene chloride and ethyl acetate (10:1) to give methyl [(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetate (31 mg).

Workup

customthe mixture was evaporated in vacuo
customThe residue was chromatographed on silica gel (1 g)
washeluting with a mixture of methylene chloride and ethyl acetate (10:1)

Sources & evidence

ORD record: ord-a0d83c36a35843f4a9ecebe4460a1d73
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04383945

Reaction notes

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