Potassium Hydroxide → HCID 70226608, compound

HRID 322912Notes

Reaction equation

HRID 322912 reaction equation
C([O:3][C:4]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:27][C:12]=2[O:13][C@@H:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:7]=1)=[O:5])C.[OH-].[K+]>CO>[OH2:3].[C:4]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=3)=[CH:27][C:12]=2[O:13][C@@H:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:7]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53717934HCID 53717934, compound

Product 1

HCID 70226608HCID 70226608, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-4-[2-(5-ethoxycarbonylpyrazol-3-yl)-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid (150 mg) in methanol (50 mL) containing 10% w/v potassium hydroxide (5 mL) is stirred at reflux for 1 hour. The reaction mixture is partitioned between 1 N acetic acid (50 mL) and ethyl acetate (50 mL). Some precipitation occurred in the organic phase which is washed with water (50 mL) and concentrated under reduced pressure. Trituration with hot ethyl acetate followed by cooling affords a solid which is filtered then washed with ethyl acetate to give (R)-4-[2-(5-carboxypyrazol-3yl)-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl) butanoic acid hydrate (40 mg) as a white solid, m.p. 144-146° C. [Elemental analysis:- C,64.1, H, 5.02, N, 8.27%. Calculated for C27H25N3O6.H2O:- C,64.2, H, 5.35, N, 8.32%].

Workup

  1. temperatureat reflux for 1 hour
  2. customThe reaction mixture is partitioned between 1 N acetic acid (50 mL) and ethyl acetate (50 mL)
  3. customSome precipitation
  4. washis washed with water (50 mL)
  5. concentrationconcentrated under reduced pressure
  6. temperatureby cooling
  7. customaffords a solid which
  8. filtrationis filtered
  9. washthen washed with ethyl acetate

Sources & evidence

ORD record
ord-1d5957e9a33846a89a9d352cabea64da
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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