1,1'-(Diazomethylene)bis(benzene) → Benzhydryl 7alpha-chloro-3-methyl-3-cephem-4-carboxylate

HRID 258011Notes

Reaction equation

HRID 258011 reaction equation
[Cl:1][C@H:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.[C:15]1([C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N+]=[N-])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:1][C@H:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([O:12][CH:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 156604937alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

Product 1

HCID 67657933Benzhydryl 7alpha-chloro-3-methyl-3-cephem-4-carboxylateYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 7α-chloro-3-methyl-3-cephem-4-carboxylic acid (10.0 g, 0.0428 mol) was dissolved in methylene chloride (200 ml), and diphenyldiazomethane (10.8 g, 0.0557 mol) dissolved in methylene chloride (50 ml) was added dropwise over 30 minutes. The mixture was stirred at room temperature for two hours. Solvent was removed under reduced pressure and the product was purified over silica column using hexane-ethyl acetate mixture to yield benzhydryl 7α-chloro-3-methyl-3-cephem-4-carboxylate (7.8 g, 45.6%). NMR (CDCl3) δ 2.1 (s, 3H, CH3), 3.25 (bs, 2H, H-2), 4.70 (bs, 1H), 4.75 (bs, 1H), 7.0 (s, 1H, CHPh2), 7.3-7.7 (m, 10H, aromatic).

Workup

  1. additionwas added dropwise over 30 minutes
  2. customSolvent was removed under reduced pressure
  3. customthe product was purified over silica column

Sources & evidence

ORD record
ord-6fc399158cfd497cb22378f14da2f744
Source dataset
uspto-grants-1993_11
Patent number
US05264429

Reaction notes

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