Water → methyl 6-cyclohexyl-5-[2-(2-methanesulfonyloxyethoxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1442548Notes

Reaction equation

HRID 1442548 reaction equation
[CH:1]1([C:7]2[C:8]3[S:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=2[O:21][CH2:22][CH2:23][OH:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41].O>C(Cl)(Cl)Cl>[CH:1]1([C:7]2[C:8]3[S:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][C:9]=3[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:13]=2[O:21][CH2:22][CH2:23][O:24][S:40]([CH3:39])(=[O:42])=[O:41])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58679111methyl 6-cyclohexyl-5-[2-(2-hydroxyethyloxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 58679107methyl 6-cyclohexyl-5-[2-(2-methanesulfonyloxyethoxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 6-cyclohexyl-5-[2-(2-hydroxyethyloxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate (628 mg, 1.41 mmol) in chloroform (10 ml) were added triethylamine (0.230 ml, 1.65 mmol) and methanesulfonyl chloride (0.120 ml, 1.55 mmol) in this order under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The obtained methyl 6-cyclohexyl-5-[2-(2-methanesulfonyloxyethoxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate was used for Step 5 without further purification.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained methyl 6-cyclohexyl-5-[2-(2-methanesulfonyloxyethoxy)-3-nitrophenyl]-4H-thieno[3,2-b]pyrrole-2-carboxylate was used for Step 5 without further purification

Sources & evidence

ORD record
ord-500d355e2c1e4e94971cb8f6d470635b
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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