Trifluoroacetic acid → HCID 11633860, compound

HRID 2100675Notes

Reaction equation

HRID 2100675 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][S:32][CH2:31][CH2:30]4)=[C:25]([CH3:35])[CH:24]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:35][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[CH:29]1[CH2:34][CH2:33][S:32][CH2:31][CH2:30]1)[O:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]([OH:36])=[O:5])[CH2:14][CH2:13]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68814793HCID 68814793, compound

Product 1

HCID 11633860HCID 11633860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 3-(4-{4-[3-Methyl-4-(tetrahydro-thiopyran-4-yl)-phenoxymethyl]-phenyl}-piperidin-1-yl)-propionic acid tert-butyl ester in dry DCM (7 mL) is added triethyl silane (5 eq., 4.442 mmol, 517 mg, 0.71 mL) followed by TFA (7 mL). The resulting mixture is stirred at room temperature for 1 hour. After concentration, the crude product is purified by preparative RP LC-MS to give 3-(4-{4-[3-methyl-4-(tetrahydro-thiopyran-4-yl)-phenoxymethyl]-phenyl}-piperidin-1-yl)-propionic acid as a tan solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.44-7.38 (m, 2H), 7.30-7.21 (m, 2H), 7.13-7.05 (m, 1H), 6.83-6.72 (m, 2H), 5.02 (s, 2H), 3.61-3.52 (m, 2H), 3.15-3.05 (m, 2H), 2.89-2.75 (m, 5H), 2.72-2.60 (m, 3H), 2.33-2.20 (m, 3H), 2.06-1.88 (m, 6H), 1.77-1.61 (m, 1H); MS (ES+): (454.2, M+1)+.

Workup

  1. concentrationAfter concentration
  2. customthe crude product is purified by preparative RP LC-MS

Sources & evidence

ORD record
ord-7a260d1bcfd34f3ea492949af7fa9a0c
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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