Hydrochloric Acid → p-Nitrobenzyl 3-oxo-7-phenoxyacetamidocepham-4-carboxylate

HRID 971523Notes

Reaction equation

HRID 971523 reaction equation
[SH:1][CH:2]1[N:5]([C:6](=[C:20]([OH:23])[CH2:21]Br)[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C:4](=[O:24])[CH:3]1[NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CO.Cl>C(Cl)Cl>[O:23]=[C:20]1[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[N:5]2[C:4](=[O:24])[CH:3]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:2]2[S:1][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86735550p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

Product 1

HCID 70547786p-Nitrobenzyl 3-oxo-7-phenoxyacetamidocepham-4-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-nitrobenzyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate prepared by the method of Example 4.--III(2) (70 mg) in a mixture of methylene chloride (2 ml), methanol (2ml), and 10% hydrochloric acid (0.3 ml) is stirred at room temperature for 2 hours. The reaction mixture is poured into ice water, and is extracted with methylene chloride. The extract solution is washed with water, dried over magnesium sulfate, and evaporated to give p-nitrobenzyl 3-oxo-7-phenoxyacetamidocepham- 4-carboxylate (44.5 mg), identical with the product of Example 4.--III(3). Yield: 74%.

Workup

  1. extractionis extracted with methylene chloride
  2. washThe extract solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-fc2b8899abb94da0a2c24e0b4678dfd3
Source dataset
uspto-grants-1979_07
Patent number
US04160085

Reaction notes

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