Hydrochloric Acid → HCID 59655976, compound

HRID 2054582Notes

Reaction equation

HRID 2054582 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][N:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:22]4[O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[C:21]=4[CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:9][C:8]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[N:7]1)C.[OH-].[K+].Cl>C1COCC1.CO>[CH:20]1[C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[O:23][C:22]=2[C:17]([C:14]2[CH:13]=[CH:12][C:11]([CH:10]3[N:6]([CH2:5][C:4]([OH:38])=[O:3])[N:7]=[C:8]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)[CH2:9]3)=[CH:16][CH:15]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59655964HCID 59655964, compound

Product 1

HCID 59655976HCID 59655976, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [5-(4-dibenzofuran-4-yl-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-acetic acid ethyl ester (0.120 g, 0.275 mmol) in THF (2 mL) and methanol (6 mL) was treated with 10% aq KOH (0.5 mL, 1 mmol) and stirred at room temperature. After 2 h, the solution was acidified with 0.5 N HCl to PH 2-3 and extracted with ethyl acetate (3×15 mL). Purification by flash column chromatography (50% ethyl acetate in heptane) provided [5-(4-dibenzofuran-4-yl-phenyl)-3-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-acetic acid (0.108 g, 95%) as a white crystalline solid.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. customPurification by flash column chromatography (50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d56e26bf9f3f4b7190a1ddaeed874fa3
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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