Diisopropylethylamine → 4-Methyl-2-{4'-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester

HRID 889719Notes

Reaction equation

HRID 889719 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[F:33][C:34]([F:46])([F:45])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[S:41](Cl)(=[O:43])=[O:42].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([S:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[C:34]([F:33])([F:45])[F:46])(=[O:43])=[O:42])[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 576660064-Methyl-2-{4'-trifluoromethyl-5-[1-(2-trifluoromethyl-benzenesulfonyl)-piperidin-3-yl]-biphenyl-3-yl}-pentanoic acid ethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (30.5 mg, 0.07mmol) in anhydrous CH2Cl2 (4 ml) was added 2-(Trifluoromethyl)benzene sulfonyl chloride (25.0 mg, 0.10 mmol) and diisopropylethylamine (24 μl, 0.14 mmol). The reaction stirred at room temperature 3 hours, was diluted with EtOAc and washed with sat. NaHCO3, and brine, dried and filtered. Purification by silica gel chromatography (Isco) gave the desired product, (35.4 mg, 79% ). Calcd for C33H35F6NO4S (M+H) 655.69, Found 656.2.

Workup

  1. washwashed with sat. NaHCO3, and brine
  2. customdried
  3. filtrationfiltered
  4. customPurification by silica gel chromatography (Isco)

Sources & evidence

ORD record
ord-450735f17c4844ca9a994f8c42c35d25
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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