Acetic Acid → HCID 88834451, compound

HRID 1287331Notes

Reaction equation

HRID 1287331 reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9]CC(Cl)(Cl)Cl)=[O:8])[N:5]1[C:16](=[O:31])[CH:17]([NH:18][C:19](=[O:30])[CH:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][CH:22]=[O:23])[C@H:4]1[S:3]2.C(O)(=O)C>CN(C)C=O.[Zn]>[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:16](=[O:31])[CH:17]([NH:18][C:19](=[O:30])[CH:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][CH:22]=[O:23])[C@H:4]1[S:3]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 88834646HCID 88834646, compound

Product 1

HCID 88834451HCID 88834451, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenyl-2-formyloxyacetamido)penam-3-carboxylate (1.52 g.) in dimethylformamide (7.5 ml.) were added acetic acid (2.3 ml.) and zinc powder (1.8 g.) under ice-cooling, and the mixture was stirred for 1 hour. After the reaction, the reaction mixture was post-treated in the similar manner as described in Example 1 to the distillation of ethyl acetate to give oily 2-methyl-2,3-methylene-6-(2-phenyl-2-formyloxyacetamido)penam-3-carboxylic acid (1.1 g.).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. additionthe reaction mixture was post-treated in the similar manner
  4. distillationas described in Example 1 to the distillation of ethyl acetate

Sources & evidence

ORD record
ord-3d39340940114619a1e9c5479653f09d
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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