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

HRID 1905283Notes

Reaction equation

HRID 1905283 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-methyoxyiminoacetamido]-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-da8063d80d294fe6968de421cd88b81b
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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