Formic Acid → 2-Chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylic acid

HRID 1395511Notes

Reaction equation

HRID 1395511 reaction equation
[Cl:1][CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10]CC(Cl)(Cl)Cl)=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1.C(O)=O>CN(C)C=O.[Zn]>[Cl:1][CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([OH:10])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 705917642-Chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylic acidYield 59.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.5 g) was dissolved in dried dimethylformamide (8 ml) and to this solution were added formic acid (1.5 ml) and then zinc powder (1.5 g) under stirring while ice-cooling. After stirring for 2 hours at the same temperature, zinc powder was filtered off and washed with dimethylformamide (5 ml). The filtrate and the washings were added to a mixed cool solution of ethylacetate (30 ml) and 5% hydrochloric acid (15 ml). After extracting with ethyl acetate, the extract was washed with water and dried over magnesium sulfate. The gummy substance (1.16 g) obtained by distilling off the solvent under reduced pressure was crystallized from a mixed solvent of ethyl acetate and isopropyl ether to give 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylic acid (660 mg) mp. 110° to 112° C. (dec.).

Workup

  1. temperaturecooling
  2. filtrationwas filtered off
  3. washwashed with dimethylformamide (5 ml)
  4. additionThe filtrate and the washings were added to a mixed
  5. temperaturecool solution of ethylacetate (30 ml) and 5% hydrochloric acid (15 ml)
  6. extractionAfter extracting with ethyl acetate
  7. washthe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customThe gummy substance (1.16 g) obtained
  10. distillationby distilling off the solvent under reduced pressure
  11. customwas crystallized from a mixed solvent of ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-8917c4386ac44d599f03adb85a3d8a85
Source dataset
uspto-grants-1980_05
Patent number
US04203897

Reaction notes

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