Triethylamine → (5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester

HRID 1351316Notes

Reaction equation

HRID 1351316 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[S:9][C:10]([C:27](=[O:29])[CH3:28])=[CH:11][C:12]=1[S:13](=[O:26])(=[O:25])[N:14]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH3:15])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Si:38](OS(C(F)(F)F)(=O)=O)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[S:9][C:10]([C:27]([O:29][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[CH2:28])=[CH:11][C:12]=1[S:13](=[O:25])(=[O:26])[N:14]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)[CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 69414947(5-Acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester

Product 1

HCID 69415031(5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester (the compound of Preparation Example 111) (946 mg) in dichloromethane (8 mL) was added triethylamine (0.58 mL) and 0.71 mL of t-butyldimethylsilyltrifluoromethane sulfonate (0.71 mL) on an ice bath. After stirring for 30 minutes, an aqueous solution of saturated sodium bicarbonate was added, and the solution was extracted with ethyl acetate. After drying the organic layer with anhydrous sodium sulfate, the residue that was obtained upon removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate) and, the title compound (985 mg) was obtained as a colorless oily matter.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  3. customthe residue that was obtained upon removal of the solvent by evaporation
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ee232449073445d9ad25b1a320fd3590
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…