Hydrochloric Acid → 3-{4-[(4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzyl)oxy]-2-fluorophenyl}propanoic acid

HRID 2110911Notes

Reaction equation

HRID 2110911 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]([CH2:18][C:19]2[CH:40]=[CH:39][C:22]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[C:27]([F:38])[CH:26]=3)=[CH:21][CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O1CCCC1.O>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:7]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[C:27]([F:38])[CH:26]=3)=[CH:39][CH:40]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23159843ethyl 3-{4-[(4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzyl)oxy]-2-fluorophenyl}propanoate

Product 1

HCID 231598663-{4-[(4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzyl)oxy]-2-fluorophenyl}propanoic acidYield 18%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The oil obtained in Example 138 was dissolved in ethanol (3 mL) and tetrahydrofuran (3 mL), and 1 N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, and neutralized with 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (Manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4) to give the title compound (91 mg, yield 18%, 2 steps) as colorless crystals. 1H NMR (CDCl3) δ: 1.32 (9H, s), 2.62 (2H, t, J=7.6 Hz), 2.68-2.76 (2H, m), 2.77-2.85 (2H, m), 2.89 (2H, t, J=7.6 Hz), 4.96 (2H, s), 5.22 (2H, s), 5.97 (1H, s), 6.59-6.66 (2H, m), 6.98-7.12 (5H, m), 7.16-7.34 (5H, m).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4)

Sources & evidence

ORD record
ord-af9a241d55684f3198b18e972b0b8bcb
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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