Trifluoroacetic acid → HCID 58920021, compound
Reaction equation
C([O:5][C:6](=[O:45])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([C@@:16]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=2)([NH:24][C:25](=[O:37])[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([C@:16]([C:11]2[CH:10]=[C:9]([CH:14]=[C:13]([F:15])[CH:12]=2)[O:8][CH2:7][C:6]([OH:45])=[O:5])([NH:24][C:25](=[O:37])[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:34])([F:35])[F:36])[CH:27]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:39][CH:40]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-tert-butyl-2-(3-(1-(5-chloropyridin-2-yl)-1-(4-fluoro-3-(trifluoromethyl)benzamido)-2-phenylethyl)-5-fluorophenoxy)acetate (27 mg, 0.04 mmol) in CH2Cl2 (1 mL) was added TFA (95 mg, 0.836 mmol). The mixture was stirred at room temperature for 2 h, and the solvent was removed to give (S)-2-(3-(1-(5-chloropyridin-2-yl)-1-(4-fluoro-3-(trifluoromethyl)benzamido)-2-phenylethyl)-5-fluorophenoxy)acetic acid as an white foam (25 mg, 100% yield). LCMS: RT=4.08 min [M+H] 591.46 (LCMS Method 1); 1H NMR (400 MHz, CDCl3) δ 3.69 (d, J=12.74 Hz, 1 H), 4.40 (d, J=13.18 Hz, 1 H), 6.53 (d, J=7.47 Hz, 3 H), 6.76 (d, J=9.23 Hz, 1 H), 6.91 (s, 1 H), 7.05 (t, J=7.47 Hz, 2 H), 7.15 (t, J=7.47 Hz, 7.25 −7.34 (m, 2 H), 7.78 (dd, J=8.57, 2.42 Hz, 1 H), 7.86 (ddd, J=8.68, 2.31, 2.20 Hz, 1 H), 7.91-7.98 (m, 1 H), 8.36 (d, J=2.20 Hz, 1 H), 9.30 (s, 1 H).
Workup
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-617dfcc1e4d84c489269e3e6941f1bdc
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888376B2
Reaction notes
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