Trifluoroacetic acid → HCID 58787658, compound

HRID 1375733Notes

Reaction equation

HRID 1375733 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:36][CH3:37])=[C:6]([C@@:8]2([F:35])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([C:21]([NH:23][C:24]([CH3:33])([CH3:32])[C:25]([O:27]C(C)(C)C)=[O:26])=[O:22])[C:9]2=[O:34])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:36][CH3:37])=[C:6]([C@@:8]2([F:35])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:19])([F:18])[F:20])=[CH:14][CH:15]=3)[N:10]([C:21]([NH:23][C:24]([CH3:33])([CH3:32])[C:25]([OH:27])=[O:26])=[O:22])[C:9]2=[O:34])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69426960HCID 69426960, compound

Product 1

HCID 58787658HCID 58787658, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 2-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)-2-methylpropanoate (Ij4): Following general procedure (G), to a solution of XVIII4 (0.24 g, 0.44 mmol) in methylene chloride (5 mL), TFA (0.34 mL, 4.4 mmol) was added. After purification by Prep. HPLC, the title compound was obtained as a white foam solid (140 mg, 65% yield). mp: 107–110° C. MS: 487 (M−H−) (very weak). Anal. Calcd. for C21H17CIF4N2O5: C, 51.60; H, 3.51; N, 5.73. Found: C, 51.29; H, 3.68; N, 5.49. 1H NMR (CDCl3): δ 1.70 (s, 3H), 1.74 (s, 3H), 3.56 (s, 3H), 6.76 (dd, J=8.8 Hz, 1.3 Hz, 1H), 7.27 (m, 1H), 7.36 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.79 (dd, J=2.5 Hz, 0.9 Hz, 1H), 8.59 (s, 1H), 8.78 (s, 1H). IR (KBr, cm−1): 3500, 3337, 1762, 1717, 1532, 1491, 1439, 1320, 1265, 1173, 1132, 1062.

Workup

  1. customAfter purification by Prep

Sources & evidence

ORD record
ord-332706173d354cc799db9e082aef266a
Source dataset
uspto-grants-2007_01
Patent number
US07169803B2

Reaction notes

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