Sodium Chloride → ethyl 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

HRID 1888312Notes

Reaction equation

HRID 1888312 reaction equation
[CH:1]1([CH2:7][C:8]([OH:30])([CH3:29])[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]([OH:28])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[CH3:38][CH3:39].[Cl-].[Na+]>CN(C)C=O>[CH:1]1([CH2:7][C:8]([OH:30])([CH3:29])[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][CH2:38][CH3:39])=[O:27])[N:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 18513229Ethane;iodideHCID 668587942-[(2-{(1R,2R,5S)-2-[(1E)-5-cyclohexyl-4-hydroxy-4-methyl-1-pentenyl]-5-hydroxycyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylic acid

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound 50 in N,N-dimethylformamide (10 mL) were added potassium carbonate (1.20 g) and ethane iodide (0.350 mL) at 0° C. and the solution was stirred at room temperature for 3 Hours. To the reaction solution was added an aqueous saturated sodium chloride solution and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (1.03 g) having the following physical data.

Workup

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

Sources & evidence

ORD record
ord-6fa9b08eea394b718b30f590a12e5a01
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

Loading…