Acetic Acid → HCID 70593017, compound

HRID 2083158Notes

Reaction equation

HRID 2083158 reaction equation
[NH:1]([CH2:8][C:9]1([CH3:35])[CH:13]([C:14]([O:16]CC(Cl)(Cl)Cl)=[O:15])[N:12]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:11]2[S:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>CN(C)C=O.[Zn]>[NH:1]([CH2:8][C:9]1([CH3:35])[CH:13]([C:14]([OH:16])=[O:15])[N:12]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:11]2[S:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70590409HCID 70590409, compound

Product 1

HCID 70593017HCID 70593017, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trichloroethyl 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.00 g) was dissolved in dimethylformamide (5 ml). To this solution were added acetic acid (0.5 ml) and then zinc powder under cooling at -15° C and the mixture was stirred for 6 hours. After the reaction, zinc powder was filtered off and the filtrate was poured into ethyl acetate. The solution was washed 4 times with water and dried over magnesium sulfate. After drying, the solvent was distilled off and the residue was dissolved in a small amount of methanol and then pulverized by adding water to the solution. The powder was collected by filtration, washed with water and dried to give 2-anilinomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylic acid (0.50 g), mp. 120° C.

Workup

  1. filtrationwas filtered off
  2. additionthe filtrate was poured into ethyl acetate
  3. washThe solution was washed 4 times with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter drying
  6. distillationthe solvent was distilled off
  7. dissolutionthe residue was dissolved in a small amount of methanol
  8. additionby adding water to the solution
  9. filtrationThe powder was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-e05d74d190854db89dc8a78a573e4d55
Source dataset
uspto-grants-1978_04
Patent number
US04084049

Reaction notes

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