Sodium Bicarbonate → HCID 53717934, compound

HRID 322911Notes

Reaction equation

HRID 322911 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:31][C:12]=2[O:13][C@@H:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH:7]=1)=[O:5])[CH3:2].C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:31][C:12]=2[O:13][C@@H:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53943755HCID 53943755, compound

Product 1

HCID 53717934HCID 53717934, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (R)-4-[2-(5-ethoxycarbonylpyrazol-3-yl)-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (1.7 g) is stirred in trifluoroacetic acid (10 mL) at ambient temperature for 15 minutes. The reaction mixture is basified with saturated sodium bicarbonate solution and a solid is precipitated which is taken up in ethyl acetate (50 mL) and washed with water (50 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated in vacuo. Recrystallisation from ethyl acetate/cyclohexane affords (R)-4-[2-(5-ethoxycarbonylpyrazol-3-yl)-5-(3-pyridylmethoxy)-phenoxy]-4-(2-methylphenyl)butanoic acid (0.35 g) in the form of a white solid, m.p. 108-110° C. [Elemental analysis:- C,67.9, H, 5.92, N, 7.64%. Calculated:- C,67.6, H, 5.63, N, 8.16%]

Workup

  1. customa solid is precipitated which
  2. washwashed with water (50 mL)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customRecrystallisation from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-a7dbfd6d6b164c36ab0b57e073224fdf
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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