Lithium Hydroxide → HCID 60152600, compound

HRID 1520917Notes

Reaction equation

HRID 1520917 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:19]3[CH:34]=[CH:33][C:22]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[O:24])=[CH:21][CH:20]=3)[CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)[CH:7]=1.O1CCCC1.[OH-].[Li+]>CO>[F:35][C:2]([F:1])([F:36])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([NH:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:24])=[CH:33][CH:34]=3)[CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68157476HCID 68157476, compound

Product 1

HCID 60152600HCID 60152600, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isomer 1 of ethyl 3-(4-(1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenylamino)butyl)benzamido)propanoate (0.300 g, 0.597 mmol) was dissolved in methanol (8.0 mL) and tetrahydrofuran (4.2 mL) and treated with 2N aqueous lithium hydroxide (4.2 mL, 8.4 mmol). The mixture was stirred at ambient temperature for 4 hours. The crude reaction mixture was concentrated and the residual solid was dissolved in water and acidified to pH=4 with 1.0M aqueous hydrochloric acid. A brown precipitate formed. The precipitate was collected by filtration, washed with water, and dried in vacuo to afford 3-(4-(1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenylamino)butyl)benzamido)propanoic acid, Isomer 1 (0.220 g, 78%) as a solid. 1H NMR (400 MHz, CDCl3, δ): 7.91 (s, 1H), 7.78 (s, 1H), 7.67 (d, J=7.6 Hz, 2H), 7.35 (d, J=6.8 Hz, 2H), 7.27 (d, J=7.2 Hz, 2H), 7.03-6.88 (m, 1H), 6.60-6.42 (m, 2H), 4.33 (t, J=6.3 Hz, 1H), 3.64 (s, 2H), 2.72-2.54 (m, 2H), 1.87-1.65 (m, 2H), 1.51-1.22 (m, 2H), 0.90 (t, J=7.0 Hz, 3H). MS (M+1): 475.2.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residual solid was dissolved in water
  4. customA brown precipitate formed
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-34bb02739285433491053901ad699d93
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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