Potassium Hydroxide → HCID 178525608, compound

HRID 2116643Notes

Reaction equation

HRID 2116643 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C@@:5]([OH:16])([C:10]1[S:14][C:13]([SH:15])=[N:12][CH:11]=1)[C:6]([F:9])([F:8])[F:7].[OH-].[K+]>C1COCC1.CO.CCOC(C)=O>[F:9][C:6]([F:7])([F:8])[C@:5]([OH:16])([C:10]1[S:14][C:13]([SH:15])=[N:12][CH:11]=1)[CH2:4][C:3]([OH:17])=[O:2]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 178500888HCID 178500888, compound

Product 1

HCID 178525608HCID 178525608, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (3S)-methyl-4,4,4-trifluoro-3-hydroxy-3-(2-mercapto-1,3-thiazol-5-yl)butanoate (enantiomer #1, 7.54 g, 26.2 mmol) in THF (80 ml) and MeOH (40 ml) was added a solution of KOH (39 ml, 2.67 N, 105 mmol). The mixture was heated at 45° C. for 4 h then cooled to room temperature. The reaction mixture was diluted in EtOAc, washed with HCl 10%, brine and dried over MgSO4. The solvent was evaporated to give the title compound in quantitative yield.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with HCl 10%, brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5b2bad138878407585d83b9a033171d0
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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