Acetic Acid → ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888297Notes

Reaction equation

HRID 1888297 reaction equation
[CH3:1][C:2]([CH3:30])([CH2:26][CH2:27][CH2:28][CH3:29])[C:3](=[O:25])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1.[BH4-].[Na+].C(O)(=O)C.O>CO>[OH:25][C@@H:3]([C:2]([CH3:1])([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:4]=[CH:5]/[C@H:6]1[CH2:10][O:9][C:8](=[O:11])[N:7]1[CH2:12][CH2:13][S:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66857555ethyl 2-[(2-{(4S)-4-[(1E)-4,4-dimethyl-3-oxo-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

Product 1

HCID 66857441ethyl 2-[(2-{(4S)-4-[(1E,3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound 6 (124 mg) in anhydrous methanol (1.40 mL) were added sodium borohydride (10.4 mg) and a catalytic amount of acetic acid at −78° C. and the solution was stirred at the same temperature for 1 hour. After return to room temperature, to the reaction solution was added water and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1), to give the title compound (87.2 mg) having the following physical data.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a8e32cd44aac4bd8aaef27881b234cc8
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

Loading…