Triethylamine → 2-[5-(1-Methanesulfonyl-piperidin-3-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester

HRID 889713Notes

Reaction equation

HRID 889713 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].[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[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:34]([CH3:33])(=[O:36])=[O:35])[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 576660362-[5-(1-Methanesulfonyl-piperidin-3-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (833 mg, 1.86 mmol) in anhydrous CH2Cl2 (27 ml) was added methanesulfonyl chloride (0.95 ml, 12.2 mmol) and Triethylamine (2.34 ml, 16.3 mmol). The reaction stirred at room temperature for 2 hours, was diluted with dichlormethane and washed with sat. NaHCO3, and brine, dried and filtered to give a yellow oil. Purification by silica gel chromatography (Isco) gave the product as an off white solid, (662 mg, 68% ). Calcd for C27H34FNO4S (M+H) 525.62, Found 526.3

Workup

  1. washwashed with sat. NaHCO3, and brine
  2. customdried
  3. filtrationfiltered
  4. customto give a yellow oil
  5. customPurification by silica gel chromatography (Isco)
  6. customgave the product as an off white solid, (662 mg, 68% )

Sources & evidence

ORD record
ord-c058b3b821764b8b95ec7167d8628813
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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