Diazomethane → 4-Nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1905288Notes

Reaction equation

HRID 1905288 reaction equation
[N+](=[CH2:3])=[N-].[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:36][OH:37])[C:11]([NH:13][CH:14]2[C:34](=[O:35])[N:16]3[C:17]([C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=4)=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1>C(OCC)C.CO>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:36][O:37][CH3:3])[C:11]([NH:13][CH:14]2[C:34](=[O:35])[N:16]3[C:17]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=4)=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 1317124954-Nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317124504-Nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diazomethane in diethyl ether was added little by little to a solution of 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 0.3 g.) in methanol (30 ml.) until the reaction terminated. The resultant solution was concentrated under reduced pressure, and the residue was pulverized with diethyl ether, collected by filtration and dried to give 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 0.26 g.) This product was identified with the authentic sample.

Workup

  1. customterminated
  2. concentrationThe resultant solution was concentrated under reduced pressure
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-32a065bbe4f44874a4e28e21accaf67a
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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