Diazomethane → 7-tert.-Butoxycarbonylamino-2-methoxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

HRID 1660376Notes

Reaction equation

HRID 1660376 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:10]1[S:11][CH2:12][C:13]([CH3:21])=[C:14]2[C:18]([OH:20])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:24])=[N-]>CCOCC>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:10]1[S:11][CH2:12][C:13]([CH3:21])=[C:14]2[C:18]([O:20][CH3:24])=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 128967587-tert.-Butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

Product 1

HCID 128967647-tert.-Butoxycarbonylamino-2-methoxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-tert.-Butoxycarbonylamino-2-methoxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-end can be prepared by esterifying 7-tert.-butoxycarbonylamino-2-carboxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (16.7 g) (described in Example 1) with a solution of diazomethane in ether, according to the method of R. B. Morin, et al., J. Amer. Soc., 91(6), 1401 (1969). 7-tert.-Butoxycarbonylamino-2-methoxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (13.6 g) is obtained in the form of white crystals (m.p.=148° C.).

Workup

  1. custom7-tert.-Butoxycarbonylamino-2-methoxycarbonyl-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-end can be prepared

Sources & evidence

ORD record
ord-4176ba7f9d7b4fc0818e81fac2f5b3e3
Source dataset
uspto-grants-1981_12
Patent number
US04307233

Reaction notes

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