Sodium Acetate → HCID 21881098, compound

HRID 724492Notes

Reaction equation

HRID 724492 reaction equation
[C:1]([S:4][C:5]1[C:10]([CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[Na+]>C(O)(C)(C)C>[C:1]([S:4][C:5]1[C:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 21881100HCID 21881100, compound

Product 1

HCID 21881098HCID 21881098, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Ten (10.0) or 100.0 mg of racemic ethyl 2-acetylthio-3-benzenepropanoate was added to 1000 μl of 90% tert-butanol and 10% 200 mM sodium acetate buffer (pH 4.0) which contained 10 mg of immobilized lipase from Mucor meihei (Novo). The glass vessel was tightly capped and stirred for 0–40 hours at room temperature. Thirty μl aliquots were-removed to ascertain conversion and optical purity. The aliquots were analyzed using an chiral HPLC column (Chiralcel AD, Daicel Chemical Industries) with a mobile phase of hexane:ethanol:trifluoroacetic acid 98:2:0.1%. The flow rate is 1 ml/minute and detection was at 230 nm. This experiment was also performed in 90% acetonitrile, acetone, and isopropanol as described above. Other racemic esters were also evaluated: butyl, isobutyl, and trifluoroethyl. The results described in Table 1 (above) were obtained.

Workup

  1. customThe glass vessel was tightly capped
  2. customThirty μl aliquots were-removed
  3. customwere obtained

Sources & evidence

ORD record
ord-851a486520b04e499f6183e4b1c0a9c4
Source dataset
uspto-grants-2006_11
Patent number
US07141694B2

Reaction notes

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