Water → HCID 13281225, compound

HRID 1679694Notes

Reaction equation

HRID 1679694 reaction equation
Cl[C:2]1[CH2:3][S:4][C@@H:5]2[CH:25]([NH:26][C:27](=[O:35])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:24](=[O:36])[N:6]2[C:7]=1[C:8]([O:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].O>C(O)(=O)C.C(Cl)Cl.[Zn]>[C:29]1([CH2:28][C:27]([NH:26][CH:25]2[C:24](=[O:36])[N:6]3[C:7]([C:8]([O:10][CH:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:9])=[CH:2][CH2:3][S:4][C@H:5]23)=[O:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 962Water2×HCID 12050113HCID 12050113, compound

Product 1

HCID 13281225HCID 13281225, compoundYield 89.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To benzhydryl 3-chloro-7-phenylacetamido-3-cephem-4-carboxylate (1.038 g) in a mixture of acetic acid (30 ml) and methylene chloride (10 ml) one adds activated zinc powder (3.9 g), stirs at room temperature for 1 hour, filters, dilutes with water, extracts with methylene chloride, washes with water, dries, concentrates, and crystallizes from ether to give benzhydryl 7-phenylacetamido-3-cephem-4-carboxylate (865 mg), m.p. 168°-170° C.

Workup

  1. additionadds
  2. customcrystallizes from ether

Sources & evidence

ORD record
ord-b4f9b6b24ec94297ac801c104c8ea29e
Source dataset
uspto-grants-1978_03
Patent number
US04081595

Reaction notes

Loading…