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

HRID 261264ノート

反応式

HRID 261264 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 6228Dimethylformamide溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-4303c5ce3ee94504bf4077522fca14fc
出典データセット
uspto-grants-1979_08
特許番号
US04164497

反応ノート

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