1,1'-(Diazomethylene)bis(benzene) → Benzhydryl 3-methyl-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylate

HRID 1702733Notes

Reaction equation

HRID 1702733 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[C:25]1([C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N+]=[N-])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:24])[N:6]2[C:7]=1[C:8]([O:10][CH:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:9]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid

Product 1

HCID 13968221Benzhydryl 3-methyl-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylateYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylic acid (17.75 g., 51 mmoles) was dissolved in 100 ml. methylene chloride. Diphenyldiazomethane (ca. 75 mmoles) was added dropwise with stirring until purple color persisted in the reaction mixture. After an additional 30 minutes of stirring at room temperature, the methylene chloride was evaporated in vacuo. The residue was taken up in a mixture of 100 ml. of water and further processed according to Preparation 4 to yield benzhydryl 3-methyl-7-(2-phenoxyacetamido)ceph-3-em-4-carboxylate [5.03 g.; pnmr (CDCl3 /TMS/delta): includes 2.0 (s, 3H), 3.2 (m, 2H), 4.5 (s, 2H), 6.9-7.6 (m, 11H)].

Workup

  1. stirringAfter an additional 30 minutes of stirring at room temperature
  2. customthe methylene chloride was evaporated in vacuo
  3. additionThe residue was taken up in a mixture of 100 ml
  4. customof water and further processed according to Preparation 4

Sources & evidence

ORD record
ord-7174d803748044edaf774b3a1ad294a1
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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