Trifluoroacetic acid → HCID 11496832, compound

HRID 2100678Notes

Reaction equation

HRID 2100678 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[C:25]([C:35]([F:38])([F:37])[F:36])[CH:24]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:29]1([C:26]2[CH:27]=[CH:28][C:23]([CH2:22][O:21][C:18]3[CH:19]=[CH:20][C:15]([CH:12]4[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]([OH:39])=[O:5])[CH2:14][CH2:13]4)=[CH:16][CH:17]=3)=[CH:24][C:25]=2[C:35]([F:38])([F:36])[F:37])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68813310HCID 68813310, compound

Product 1

HCID 11496832HCID 11496832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{4-[4-(4-Cyclohexyl-3-trifluoromethyl-benzyloxy)-phenyl]-piperidin-1-yl}-propionic acid tert-butyl ester is dissolved in DCM and treated with TFA (50% v/v). After 2 h at room temperature, it is concentrated to give a residue which is purified by RP LC-MS to give 3-{4-[4-(4-Cyclohexyl-3-trifluoromethyl-benzyloxy)-phenyl]-piperidin-1-yl}-propionic acid. 1HNMR (400 MHz, CD3OD) δ 7.83 (1H, s), 7.65 (1H, d), 7.55 (1H, d), 7.20 (4H, m), 5.45 (2H, s), 3.66 (2H, d), 3.44 (2H, m), 3.20 (2H, m), 2.81 (2H, m), 2.68 (2H, m), 1.84 (9H, m), 1.36 (5H, m). MS (ES+): 490.3 (M+1)+.

Workup

  1. concentrationit is concentrated
  2. customto give a residue which
  3. customis purified by RP LC-MS

Sources & evidence

ORD record
ord-52c04f473ee94ab895dd5556310da43f
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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