Trifluoroacetic acid → 4-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid methyl ester

HRID 1178944Notes

Reaction equation

HRID 1178944 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17](=[O:43])[C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([C:36]3(O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:28]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>CCOC(C)=O>[CH3:15][O:16][C:17](=[O:43])[C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([CH:36]3[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]3)=[CH:28]2)(=[O:25])=[O:26])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 589750254-[3-(1-Hydroxy-cyclohexyl)-indole-1-sulfonyl]-benzoic acid methyl ester

Product 1

HCID 589752204-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under N2, add triethylsilane (676 mg, 0.929 ml, 5.82 mmol, 2.6 eq) followed by trifluoroacetic acid (4.08 g, 2.7 ml, 35.79 mmol, 16.0 eq) to a CH2CL2 solution (20 ml) of 4-[3-(1-Hydroxy-cyclohexyl)-indole-1-sulfonyl]-benzoic acid methyl ester (925 mg, 2.24 mmol, 1 eq). Stir for 1.5 hours and then remove volatiles on rotovap. Add EtOAc to crude mix and workup with sat aqueous sodium bicarbonate. Extract product into organics, separate organics, dry over MgSO4, and concentrate on rotovap to give crude product as a pink oil. Purify by silica gel chromatography to give 4-(3-Cyclohexyl-indole-1-sulfonyl)-benzoic acid methyl ester (775 mg, 87% yield) as a white solid. Mass Spectrum (m/e): 397.99 (MH+).

Workup

  1. customExtract product into organics, separate organics
  2. dry with materialdry over MgSO4
  3. concentrationconcentrate on rotovap
  4. customto give crude product as a pink oil
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-91a319a362c945f89e82beb08f6ffd16
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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