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 1981212Notes

Reaction equation

HRID 1981212 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1061PhosphateSolventHCID 3283Diethyl EtherSolvent

Procedure

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)].

Workup

  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

Sources & evidence

ORD record
ord-4207c377e9e444f7a7d6671bfc98a951
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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