Diazomethane → HCID 12784140, compound

HRID 2420541Notes

Reaction equation

HRID 2420541 reaction equation
[N+](=[CH2:3])=[N-].[N+:4]([C:7]1[CH:37]=[CH:36][C:10]([CH2:11][O:12][C:13]([C:15]2[N:20]3[C:21](=[O:34])[C@@H:22]([NH:23][C:24](=[O:33])[CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:19]3[S:18][CH2:17][C:16]=2[OH:35])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5]>C(Cl)(Cl)Cl>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][O:12][C:13]([C:15]2[N:20]3[C:21](=[O:34])[C@@H:22]([NH:23][C:24](=[O:33])[CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:19]3[S:18][CH2:17][C:16]=2[O:35][CH3:3])=[O:14])=[CH:36][CH:37]=1)([O-:6])=[O:5]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 547167947beta-Phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester

Product 1

HCID 12784140HCID 12784140, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3 ml of an ethereal diazomethane solution (0.5 molar, 1.5 equivalents) are added in the course of about 10 minutes to a solution, cooled to 0° C, of 485 mg of 7β-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester in 10 ml of dry chloroform. The pale yellow solution is stirred for 1 hour at 0° C, flushed with nitrogen in order to remove excess diazomethane and concentrated in vacuo. The residue is recrystallized from methylene chloride and gives 7β-phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester of melting point 140.5°-142° C.

Workup

  1. customflushed with nitrogen in order
  2. customto remove excess diazomethane
  3. concentrationconcentrated in vacuo
  4. customThe residue is recrystallized from methylene chloride

Sources & evidence

ORD record
ord-f587f6df83f74cef9e7846a7989e9577
Source dataset
uspto-grants-1978_08
Patent number
US04110533

Reaction notes

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