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 1981212ノート

反応式

HRID 1981212 の反応式
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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 1061Phosphate溶媒HCID 3283Diethyl Ether溶媒

実験手順

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)].

後処理

  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

出典と根拠

ORDレコード
ord-4207c377e9e444f7a7d6671bfc98a951
出典データセット
uspto-grants-1985_04
特許番号
US04512999

反応ノート

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