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

HRID 848366Notes

Reaction equation

HRID 848366 reaction equation
[N+](=[CH2:3])=[N-].[Br:4][CH2:5][C:6]([C:8](=[N:34][OH:35])[C:9]([NH:11][CH:12]1[C:32](=[O:33])[N:14]2[C:15]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)=[O:20])=[CH:16][CH2:17][S:18][C@H:13]12)=[O:10])=[O:7]>C(OCC)C.O1CCCC1>[Br:4][CH2:5][C:6]([C:8](=[N:34][O:35][CH3:3])[C:9]([NH:11][CH:12]1[C:32](=[O:33])[N:14]2[C:15]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)=[O:20])=[CH:16][CH2:17][S:18][C@H:13]12)=[O:10])=[O:7]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 178520134HCID 178520134, compound

Product 1

HCID 1317124944-Nitrobenzyl 7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diazomethane in diethyl ether was added little by little to a solution of 4-nitrobenzyl 7-[2-(2-bromoacetyl)-2-hydroxyiminoacetamido]-3-cephem-4-carboxylate (0.9 g.) in tetrahydrofuran (30 ml.) under ice-cooling until the reaction terminated, and then acetic acid was added to the resultant solution to decompose excess diazomethane. The resultant solution was concentrated under reduced pressure to give the foamy product of 4-nitrobenzyl 7-[2-(2-bromoacetyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer: 0.9 g.).

Workup

  1. temperaturecooling until the reaction
  2. customterminated
  3. additionacetic acid was added to the resultant solution
  4. concentrationThe resultant solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-414cb92d473947599132c0d8dd55325c
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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