Diazomethane → 2-[4-(p-Toluenesulphonylthio)-3-(alpha-tert.butoxycarbonylamino-alpha-phenylacetylamino)-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

HRID 26108Notes

Reaction equation

HRID 26108 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:54])/[C:16](/[N:20]2[CH:23]([S:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:22]([NH:35][C:36](=[O:52])[CH:37]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:21]2=[O:53])=[C:17](\[OH:19])/[CH3:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:57])=[N-]>C(Cl)Cl.CO.CCOCC>[C:1]1([CH:7]([O:14][C:15](=[O:54])/[C:16](/[N:20]2[CH:23]([S:24][S:25]([C:28]3[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=3)(=[O:27])=[O:26])[CH:22]([NH:35][C:36](=[O:52])[CH:37]([NH:44][C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:21]2=[O:53])=[C:17](\[O:19][CH3:57])/[CH3:18])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 705588652-[4-(p-Toluenesulphonylthio)-3-(alpha-tert.butoxycarbonylamino-alpha-phenylacetylamino)-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester

Product 1

HCID 705580452-[4-(p-Toluenesulphonylthio)-3-(alpha-tert.butoxycarbonylamino-alpha-phenylacetylamino)-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 0.54 g (0.7 mmol) of 2-[4-(p-toluenesulphonylthio)-3-(α-tert.butoxycarbonylamino-α-phenylacetylamino)-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester in 20 ml of methylene chloride/methanol, 1:1, is stirred for 15 minutes with an excess of a solution of diazomethane in ether at 0° C. and is then concentrated by evaporation in vacuo. Preparative layer chromatography of the residue on silica gel, using toluene/ethyl acetate, 1:1, as the running agent, and elution of the zone which is visible in UV light gives 2-[4-(p-toluenesulphonylthio)-3-(α-tert.butoxycarbonylamino-α-phenylacetylamino)-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester, which is recrystallised from methylene chloride/diethyl ether/hexane.

Workup

  1. concentrationis then concentrated by evaporation in vacuo
  2. washas the running agent, and elution of the zone which

Sources & evidence

ORD record
ord-63e3f94090f34f9a8e30e9acc03f6c32
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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