Water → ethyl 2-[(2-{(1R,2R)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888313Notes

Reaction equation

HRID 1888313 reaction equation
[CH:1]1([CH2:7][C:8]([OH:32])([CH3:31])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH:1]1([CH2:7][C:8]([OH:32])([CH3:31])[CH2:9]/[CH:10]=[CH:11]/[C@H:12]2[CH2:16][CH2:15][C:14](=[O:17])[C@@H:13]2[CH2:18][CH2:19][S:20][C:21]2[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 68771064ethyl 2-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxyl ate

Product 1

HCID 66858314ethyl 2-[(2-{(1R,2R)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylateYield 63.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the compound 51 (242 mg) in dimethylsulfoxide (2.0 mL)/ethyl acetate (4.0 mL) were added diisopropylethylamine (0.70 mL) and sulfur trioxide-pyridine complex (320 mg) at 10° C. and the solution was stirred for 30 minutes. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed 1N hydrochloric acid, water and brine, anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3) to give the title compound (154 mg) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed 1N hydrochloric acid, water and brine, anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-1df9d3c584214626b3140450fe33a498
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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