Sodium 2-ethylhexanoate → sodium (2S,5R)-3,3-dimethyl-6-(3-methyl-2-oxobutylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

HRID 1981212노트

반응식

HRID 1981212 반응식
C(O)(=O)C(C)(C)C.C=[S:9]1[C@H:15]2[N:12]([C:13](=[O:22])[C:14]2=[CH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[C@@H:11]([C:23]([OH:25])=[O:24])[C:10]1([CH3:27])[CH3:26].C(C(CCCC)C([O-])=O)C.[Na+:38]>CS(C)=O.P([O-])([O-])([O-])=O.CCOCC>[CH3:27][C:10]1([CH3:26])[S:9][C@H:15]2[N:12]([C:13](=[O:22])[C:14]2=[CH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[C@H:11]1[C:23]([O-:25])=[O:24].[Na+:38]

참가 물질

6

반응물 2

HCID 23672331Sodium 2-ethylhexanoateHCID 86740050methylene-(2S,5R)-3,3-dimethyl-6-(3-methyl-2-oxobutylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

생성물 1

HCID 70482142sodium (2S,5R)-3,3-dimethyl-6-(3-methyl-2-oxobutylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 1061Phosphate용매HCID 3283Diethyl Ether용매

실험 절차

A suspension of 2.2 g of methylene-(2S,5R)-3,3-dimethyl-6-(3-methyl-2-oxobutylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 300 ml of dimethyl sulphoxide and 500 ml of phosphate buffer (pH 7.1) is treated at 20° with 2 ml of a suspension of pig liver esterase (3 mg/ml). The reaction mixture is stirred at 20° for 2 hours and subsequently extracted with ether. The aqueous phase is acidified (pH 3.2) with 50% citric acid and extracted with ether. The organic extract is washed with distilled water, dried over magnesium sulphate, filtered and evaporated. There is obtained an oily residue which is dissolved in 200 ml of ether and treated with 2.4 ml of a 2M solution of sodium 2-ethylcaproate. The crystalline precipitate is filtered off under suction, washed with ether and dried over phosphorus pentoxide in vacuo. There is obtained sodium (2S,5R)-3,3-dimethyl-6-(3-methyl-2 -oxobutylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate of melting point 145° (decomposition). [Rf : 0.41; chloroform/ethyl acetate/acetic acid (5:4:1); NMR (D2O) δ (ppm); 1.17 (6H); 1.53 (3H); 1.61 (3H); 2.95 (1H); 4.4 (1H); 6.05 (1H); 6.9 (1H)].

후처리

  1. extractionsubsequently extracted with ether
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washis washed with distilled water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThere is obtained an oily residue which
  9. filtrationThe crystalline precipitate is filtered off under suction
  10. washwashed with ether
  11. dry with materialdried over phosphorus pentoxide in vacuo

출처 및 근거

ORD 기록
ord-4207c377e9e444f7a7d6671bfc98a951
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04512999

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