Trifluoroacetic acid → HCID 60151936, compound

HRID 537520Notes

Reaction equation

HRID 537520 reaction equation
C([N:5]([CH2:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[N:25]3)=[CH:20][CH:19]=2)[CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:15][CH:14]([CH3:16])[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[CH:8][CH:9]=1)[O:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[N:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157427HCID 68157427, compound

Product 1

HCID 60151936HCID 60151936, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of tert-butyl 3-(N-tert-butyl-4-(2-methyl-1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)propyl)benzamido)propanoate (60 mg, 0.10 mmol) in dichloromethane (6 mL) was added trifluoroacetic acid (2.0 mL). The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and purification by HPLC gave (+/−)-3-(4-(2-methyl-1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)propyl)benzamido)propanoic acid (11.4 mg, 24%). 1H NMR (400 MHz, CD3OD, δ): 8.53 (s, 1H), 7.89 (s, 1H), 7.76 (d, 2H), 7.55 (d, 2H), 7.45 (d, 2H), 6.97 (d, 2H), 5.06 (d, 1H), 3.61-3.58 (m, 2H), 2.62-2.59 (m, 2H), 2.21-2.11 (m, 1H), 1.08 (d, 3H), 0.93 (d, 3H). MS (M+1): 476.4.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurification by HPLC

Sources & evidence

ORD record
ord-de99b125ec2447e2bc005fc499cd0987
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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