Lithium Hydroxide → 3-(3-{3-t-Butyl-5-[3-(4-fluoro-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid

HRID 491996Notes

Reaction equation

HRID 491996 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[O:20])=[CH:16][C:15]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:14]2)[CH:8]=1)C.[Li+].[OH-]>CO>[C:29]([C:15]1[CH:16]=[C:17]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[O:20])[N:13]([C:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:33])=[O:3])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 588428503-(3-{3-t-Butyl5-[3-(4-fluoro-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid ethyl ester

Product 1

HCID 160713723-(3-{3-t-Butyl-5-[3-(4-fluoro-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 145 (45 mg, 0.1 mmol) and 2N LiOH (3 mL) in MeOH (3 mL) was stirred at RT overnight. The reaction mixture was neutralized to pH=4, extracted with ethyl acetate (3×20 mL), the combined organic extracts were washed with brine, dried (NaSO4) and filtered. The filtrate was concentrated to afford 3-(3-{3-t-butyl-5-[3-(4-fluoro-phenyl)-ureido]-pyrazol-1-yl}-phenyl)-propionic acid, (37 mg, 90%). 1H NMR (CD3OD): 7.63-7.62 (m, 2H), 7.56 (s, 1H), 7.53-7.48 (m, 1H), 7.41-7.38 (m, 2H), 7.04 (t, J=8.8 Hz, 2H), 5.49 (s, 1H), 3.07 (t, J=7.6 Hz, 2H), 2.72 (t, J=7.6 Hz, 2H), 1.42 (s, 9H); MS (ESI) m/z: 415 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f4a3c107d6514b15b1d0911de24d037c
Source dataset
uspto-grants-2009_05
Patent number
US07531566B2

Reaction notes

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