Water → 2-Benzhydryloxycarbonyl-7-(4-bromo-2-methoxyimino-3-oxo-butyrylamino)-8-oxo-3-(2-tosyloxy-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660397Notes

Reaction equation

[Br:1][CH2:2][C:3](=[O:11])[C:4](=[N:8][O:9][CH3:10])[C:5](Cl)=[O:6].[NH2:12][CH:13]1[C:20](=[O:21])[N:19]2[CH:14]1[S:15][CH2:16][C:17]([CH:38]=[CH:39][O:40][S:41]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)(=[O:43])=[O:42])=[C:18]2[C:22]([O:24][CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].O.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH:25]([O:24][C:22]([C:18]1[N:19]2[CH:14]([S:15][CH2:16][C:17]=1[CH:38]=[CH:39][O:40][S:41]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)(=[O:43])=[O:42])[CH:13]([NH:12][C:5](=[O:6])[C:4](=[N:8][O:9][CH3:10])[C:3](=[O:11])[CH2:2][Br:1])[C:20]2=[O:21])=[O:23])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 4-bromo-2-methoxyimino-3-oxo-butyryl chloride syn isomer (2 g) in acetone (10 cc) is added, in the course of 7 minutes, to a solution, cooled to -10° C., of 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxy-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene, E-form (4.7 g) in acetone (50 cc), water (5 cc) and sodium bicarbonate (2.8 g). The mixture is stirred for 1 hour at -10° C. and is then concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). Crude 2-benzhydryloxycarbonyl-7-(4-bromo-2-methoxyimino-3-oxo-butyrylamino)-8-oxo-3-(2-tosyloxy-vinyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (syn isomer, E-form) (11 g) is obtained.

Workup

concentrationis then concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)

Sources & evidence

ORD record: ord-8937e04170cb4a66b7a4796b6da914e4
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04307230

Reaction notes

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