1,1'-(Diazomethylene)bis(benzene) → 2-Benzhydryloxycarbonyl-7-tert.-butoxycarbonylamino-3-methylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]octane

HRID 1660375Notes

Reaction equation

HRID 1660375 reaction equation
[C:1]([CH:4]1[C:11](=[CH2:12])[CH2:10][S:9][CH:8]2[N:5]1[C:6](=[O:21])[CH:7]2[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([OH:3])=[O:2].[C:22]1([C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N+]=[N-])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH:28]([O:2][C:1]([CH:4]1[C:11](=[CH2:12])[CH2:10][S:9][CH:8]2[N:5]1[C:6](=[O:21])[CH:7]2[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[O:3])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 128967732-Carboxy-7-tert.-butoxycarbonylamino-3-methylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]octane

Product 1

HCID 128967752-Benzhydryloxycarbonyl-7-tert.-butoxycarbonylamino-3-methylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]octaneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Carboxy-7-tert.-butoxycarbonylamino-3-methylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]octane (21.3 g) is esterified with diphenyldiazomethane (11.2 g) in accordance with the procedure of Example 1. 2-Benzhydryloxycarbonyl-7-tert.-butoxycarbonylamino-3-methylene-8-oxo-5-thia-1-aza-bicyclo[4.2.0]octane (18.35 g) is obtained in the form of white crystals (m.p.=135°-7° C. after recrystallisation from ethyl acetate).

Sources & evidence

ORD record
ord-a0d44ef5d61644aa84636dc9c5cc8414
Source dataset
uspto-grants-1981_12
Patent number
US04307233

Reaction notes

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