Acetic Acid → HCID 68132226, compound

HRID 1287329Notes

Reaction equation

HRID 1287329 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:28])[CH:17]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[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:28])[CH:17]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C@H:4]1[S:3]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68131967HCID 68131967, compound

Product 1

HCID 68132226HCID 68132226, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(3-phenylureido)penam-3-carboxylate (1.12 g.) in dimethylformamide (7.5 ml.) were added acetic acid (2.3 ml.) and then 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 and residue obtained by distilling off ethyl acetate was crystallized by adding a small amount of acetonitrile to give colorless crystals of 2-methyl-2,3-methylene-6-(3-phenylureido)penam-3-carboxylic acid (0.72 g.), mp 108° to 110°C.

Workup

  1. customAfter the reaction
  2. additionthe reaction mixture was post-treated in the similar manner
  3. customobtained
  4. distillationby distilling off ethyl acetate
  5. customwas crystallized
  6. additionby adding a small amount of acetonitrile

Sources & evidence

ORD record
ord-c99a9adef91f4b8d8b56185d678d52a5
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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