Tert-Butylamine → HCID 131725065, compound

HRID 585150Notes

Reaction equation

HRID 585150 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C:8]2([F:36])[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][P:23](=[O:34])([O:29]C(C)(C)C)[O:24]C(C)(C)C)[C:9]2=[O:35])[CH:7]=1.FC(F)(F)C(O)=O.[C:46]([NH2:50])([CH3:49])([CH3:48])[CH3:47]>ClCCl>[C:46]([NH2+:50][C:6]([CH3:8])([CH3:7])[CH3:5])([CH3:49])([CH3:48])[CH3:47].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C@@:8]2([F:36])[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][P:23](=[O:24])([O-:29])[O-:34])[C:9]2=[O:35])[CH:7]=1.[C:46]([NH2+:50][C:6]([CH3:8])([CH3:7])[CH3:5])([CH3:49])([CH3:48])[CH3:47]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 6422Trifluoroacetic acidHCID 20822776HCID 20822776, compound

Product 1

HCID 131725065HCID 131725065, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flask containing phosphoric acid di-tert-butyl ester 3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-ylmethyl ester ((S)-III) (0.500 g, 0.860 mmol) was added 10 mL anhydrous dichloromethane, and trifluoroacetic acid (0.196 g, 1.72 mmol). The reaction was allowed to stir at room temperature for 24 hours. The dichloromethane was evaporated in vacuo, and the crude foam was purified by reverse phase chromatography (C18 2:1CH3CN:H2O), then the isolated free phosphate was dissolved in ethyl acetate and t-butyl amine (0.251 g, 3.44 mmol) was added and the solvent was evaporated in vacuo producing the title compound (0.100 g, 19%) as a white powder. 1H NMR (D2O 500 MHz): δ=7.89 (s, 1H), 7.78 (s, 1H), 7.50 (m, 2H), 7.41 (d, 1H, J=6.4 Hz), 7.03 (d, 1H, J=6.4 Hz), 5.63 (dd, 1H, J=12.0, 6.8 Hz), 5.56 (dd, 1H, J=12.0, 6.8 Hz), 3.56 (s, 3H), 1.36 (s, 18H); 31P NMR (D2O 202 MHz) δ=1.68; LRMS [M−H]−467.9.

Workup

  1. customThe dichloromethane was evaporated in vacuo
  2. customthe crude foam was purified by reverse phase chromatography (C18 2:1CH3CN:H2O)
  3. dissolutionthe isolated free phosphate was dissolved in ethyl acetate
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e9934eaec49d4bb2adff6cf98b8910fb
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

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