Triethylamine → 4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxo-azetidin-2-yl]-3-oxobutanoate

HRID 235751Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:6]1[C:9](=[O:10])[NH:8][C@@H:7]1[CH2:11][C:12](=[O:27])[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])([CH3:5])[CH3:4].C1(C)C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1.C(N(CC)CC)C>C(#N)C>[N+:37](=[C:13]([C:12](=[O:27])[CH2:11][C@@H:7]1[C@@H:6]([C:3]([O:2][CH3:1])([CH3:5])[CH3:4])[C:9](=[O:10])[NH:8]1)[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)=[O:15])=[N-:38]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoate (61.2 mg) in acetonitrile (1.22 ml) was added a solution of p-toluenesulfonyl azide (38.3 mg) in acetonitrile (0.345 ml) at 0° C. After stirring for 10 minutes at 0° C., a solution of triethylamine (81.3 μl) in acetonitrile (0.732 ml) was added dropwise at 0° C. After the resultant solution was stirred for 30 minutes at 0° C., the solvent was distilled off, and the residue was flash-chromatographed on silica gel (0.9 g) eluting with a mixture of methylene chloride and ethyl acetate (40:1 to 3:1) to give 4-nitrobenzyl 2-diazo-4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]-3-oxobutanoate (56.5 mg) as an amorphous solid.

Workup

distillationthe solvent was distilled off
customthe residue was flash-chromatographed on silica gel (0.9 g)
washeluting with a mixture of methylene chloride and ethyl acetate (40:1 to 3:1)

Sources & evidence

ORD record: ord-06de43affb7c4efe8ca402bb83267e55
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640915

Reaction notes

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