Trifluoroacetic acid → HCID 10218265, compound

HRID 585163Notes

Reaction equation

HRID 585163 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:42][CH3:43])=[C:6]([C@@:8]2([F:41])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][O:22][C:23](=[O:39])[CH2:24][CH2:25][O:26][P:27]([O:34]C(C)(C)C)([O:29]C(C)(C)C)=[O:28])[C:9]2=[O:40])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:42][CH3:43])=[C:6]([C@@:8]2([F:41])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][O:22][C:23](=[O:39])[CH2:24][CH2:25][O:26][P:27]([OH:34])([OH:29])=[O:28])[C:9]2=[O:40])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69337653HCID 69337653, compound

Product 1

HCID 10218265HCID 10218265, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL flask containing (S)-3-(di-tert-butoxy-phosphoryloxy)-propionic acid 3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-ylmethyl ester ((S)-XVII, n=1) (0.144 g, 0.22 mmol) was added 2 mL anhydrous dichloromethane, and trifluoroacetic acid (0.075 g, 0.66 mmol). The reaction was allowed to stir at room temperature for 4 hours. The dichloromethane was evaporated in vacuo, and the crude foam was purified by reverse phase chromatography (C18 2:1CH3CN:H2O) producing the title compound (0.070 g, 59%) as a white powder. 1H NMR (CDCl3 400 MHz): δ=7.70 (s, 1H), 7.36 (s, 1H), 7.32-7.27 (m, 3H), 7.20 (d, 1H, J=6 Hz), 6.73 (d, 1H, J=8 Hz), 5.91 (d, 1H, J=11.2 Hz), 5.73 (d, 1H, J=11.2 Hz), 4.27 (m, 2H), 3.44 (s, 3H), 2.75 (m, 2H); 31P NMR (CDCl3 162 MHz) δ=1.15; 19F NMR (CDCl3 376 MHz) δ=−63.2, −159.4; LRMS [M−H]−539.89, [M+NH4]+564.1.

Workup

  1. customThe dichloromethane was evaporated in vacuo
  2. customthe crude foam was purified by reverse phase chromatography (C18 2:1CH3CN:H2O)

Sources & evidence

ORD record
ord-00e5671bb6d348d88ae54ebd828de58a
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

Loading…