HCID 53897661, compound → HCID 54275016, compound

HRID 322913Notes

Reaction equation

HRID 322913 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:30][C:11]=2[O:12][C@@H:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH:6]=1)=[O:4]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]([C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:30][C:11]=2[O:12][C@@H:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:6]=1)=[O:4]

Participants

3

Reactant 1

HCID 53897661HCID 53897661, compound

Product 1

HCID 54275016HCID 54275016, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (R)-4-[2-(5-methoxycarbonylpyrazol-3-yl)-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (2 g) is dissolved in trifluoroacetic acid (10 mL) and allowed to stand at room temperature for 2 minutes. The solution is quenched with saturated aqueous sodium hydrogen carbonate solution (100 mL) and the product extracted into ethyl acetate (100 mL). This solution is washed with water, dried, and evaporated. The residue is purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and cyclohexane (3:2 v/v) to remove trace high running impurities, and then eluting with a mixture of methanol and dichloromethane (1:4 v/v). Fractions heterogeneous in the required product are combined and evaporated. The residue is recrystallised from a mixture ethyl acetate and cyclohexane to give (R)-4-[2-(5-methoxycarbonylpyrazol-3-yl)-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid (0.4 g) as a white solid, m.p. 155-156° C. [Elemental analysis:- C,66.90; H,5.49; N,8.11%. Calculated:- C,67.00; H,5.43; N,8.43%].

Workup

  1. customThe solution is quenched with saturated aqueous sodium hydrogen carbonate solution (100 mL)
  2. extractionthe product extracted into ethyl acetate (100 mL)
  3. washThis solution is washed with water
  4. customdried
  5. customevaporated
  6. customThe residue is purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and cyclohexane (3:2 v/v)
  7. customto remove trace high running impurities
  8. washeluting with a mixture of methanol and dichloromethane (1:4 v/v)
  9. customevaporated
  10. customThe residue is recrystallised from a mixture ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-c53f730e1d6b4eb6a31d00a33a6307bc
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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