Lithium Hydroxide → 3-(3-{3-t-Butyl-5-[(pyridine-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid

HRID 492023Notes

Reaction equation

HRID 492023 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:20])=[CH:16][C:15]([C:27]([CH3:30])([CH3:29])[CH3:28])=[N:14]2)[CH:8]=1)C.[Li+].[OH-]>CO>[C:27]([C:15]1[CH:16]=[C:17]([NH:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:20])[N:13]([C:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58842928HCID 58842928, compound

Product 1

HCID 184498963-(3-{3-t-Butyl-5-[(pyridine-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acidYield 76.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 151 (42 mg, 0.1 mmol) and 2N LiOH (3 mL) in MeOH (3 mL) was stirred at RT over night. The reaction mixture was neutralized to pH=4, and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine, dried (Na2SO4), and filtered. The filtrate was concentrated to afford 3-(3-{3-t-butyl-5-[(pyridine-2-carbonyl)-amino]-pyrazol-1-yl}-phenyl)-propionic acid (30 mg, 76%). 8.45 (d, 4.0 Hz, 1H), 8.24 (d, 8.0 Hz, 1H), 7.92 (s, 1H), 7.88 (t, 7.6 Hz, 1H), 7.67 (d, 8.0 Hz, 1H), 7.36 (t, 5.6 Hz, 1H), 7.23 (t, 7.6 Hz, 1H), 6.96 (d, 6.8 Hz, 1H), 6.67 (s, 1H), 2.77 (t, 7.6 Hz, 2H), 2.22 (t, 7.6 Hz, 2H), 1.26 (s, 9H); MS (ESI) m/z: 393 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e23689be607944c099a2c1e59b54bb23
Source dataset
uspto-grants-2009_05
Patent number
US07531566B2

Reaction notes

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