Lithium Hydroxide → HCID 58920585, compound

HRID 1365525Notes

Reaction equation

HRID 1365525 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([NH:38][C:39](=[O:51])[C:40]2[CH:45]=[CH:44][C:43]([F:46])=[C:42]([C:47]([F:50])([F:49])[F:48])[CH:41]=2)([C:24]2[CH:29]=[C:28]([O:30][C:31]([F:36])([F:35])[CH:32]([F:34])[F:33])[CH:27]=[C:26]([F:37])[CH:25]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[Li+].[OH-]>C1COCC1.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([NH:38][C:39](=[O:51])[C:40]2[CH:45]=[CH:44][C:43]([F:46])=[C:42]([C:47]([F:50])([F:48])[F:49])[CH:41]=2)([C:24]2[CH:29]=[C:28]([O:30][C:31]([F:36])([F:35])[CH:32]([F:33])[F:34])[CH:27]=[C:26]([F:37])[CH:25]=2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86613589HCID 86613589, compound

Product 1

HCID 58920585HCID 58920585, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-ethyl 4-(4-(2-(5-chloropyridin-2-yl)-2-(4-fluoro-3-(trifluoromethyl)benzamido)-2-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)ethyl)phenyl)butanoate (11.2 mg, 0.015 mmol) was dissolved in THF (0.2 mL) and a 1N LiOH solution was added. The reaction mixture was stirred at room temperature for 3 days, then diluted with 1N HCl (0.5 mL). The aqueous layer was extracted with CH2Cl2 (3×0.5 mL). The combined organic portions were dried over Na2SO4, filtered and the solvent removed in vacuo to yield (S)-4-(4-(2-(5-chloropyridin-2-yl)-2-(4-fluoro-3-(trifluoromethyl)benzamido)-2-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)ethyl)phenyl)butanoic acid (9.9 mg, 92% yield) as a clear film. LCMS: RT=1.55 min [M+H] 719.0 (LCMS Method 2) NMR: 400 MHz 1H (CDCl3) 9.02 ppm, 1H, s; 8.29 ppm, 1H, d, J=2.20 Hz; 7.94 ppm, 1H, m; 7.80 ppm, 1H, m; 7.67 ppm, 1H, dd, J=2.42 and 8.57 ppm, 7.13 ppm, 1H, d, J=8.79 Hz; 7.05 ppm, 2H, m; 6.84 ppm, 1H, d, J=8.79 Hz; 6.77 ppm, 2H, d, J=7.91 Hz; 6.38 ppm, 2H, J=7.91 Hz; 5.81 ppm, 1H, tt, J=2.63 and 52.73 Hz; 4.44 ppm, 1H, d, J=12.74 Hz; 3.51 ppm, 1H, d, J=12.74 Hz; 2.47 ppm, 2H, t, J=7.69 Hz; 2.22 ppm, 2H, t, J=7.25 Hz; 1.80 ppm, 2H, m.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×0.5 mL)
  2. dry with materialThe combined organic portions were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5662c633469a453ca7baaff830d4b25c
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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