Lithium Hydroxide → HCID 86687976, compound

HRID 509368Notes

Reaction equation

HRID 509368 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)=[O:22])[C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.C1COCC1.[Li+].[OH-]>CO>[F:33][C:2]([F:1])([F:34])[C:3]1[CH:4]=[CH:5][C:6]([C@H:9]([NH:20][C:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[O:22])[C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86687977HCID 86687977, compound

Product 1

HCID 86687976HCID 86687976, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 4-(((4-(trifluoromethyl)phenyl)(3-(trifluoro-methyl)pyridin-2-yl)methyl)carbamoyl)benzoate (135 mg, 0.280 mmol, Example 140) and THF (7 mL):MeOH (3 mL) was added 1M LiOH (1 mL, 1.000 mmol). After 2 h, the reaction was concentrated in vacuo. The off-white solid was taken up in a minimum of DCM and eluted through a Redi-Sep® pre-packed silica gel column (4 g) with EtOAc to provide the title compound as a white solid. 1H NMR (CD3OD, 300 MHz) δ ppm 8.91 (d, J=4.8 Hz, 1H), 8.18 (d, J=7.9 Hz, 1H), 8.03 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.53-7.66 (m, 5H), 6.93 (s, 1H). MS (ESI pos. ion) m/z: 469.0 (M+H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. washeluted through a Redi-Sep® pre-packed silica gel column (4 g) with EtOAc

Sources & evidence

ORD record
ord-8cdef6fcce0c482ab3be489169218d60
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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