Hydrochloric Acid → HCID 23157637, compound

HRID 508067Notes

Reaction equation

HRID 508067 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:16]=[C:17]([CH:34]=[CH:35][C:36]=2[O:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[C:22]([F:33])[CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>C(OCC)(=O)C.O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:11])([CH3:13])[CH3:12])[N:7]([CH2:14][C:15]2[CH:16]=[C:17]([CH:34]=[CH:35][C:36]=2[O:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:22]([F:33])[CH:21]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 23157418HCID 23157418, compound

Product 1

HCID 23157637HCID 23157637, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 3-[4-({3-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]-4-isobutoxybenzyl}amino)-2-fluorophenyl]propanoate (0.62 g, 1.16 mmol), methanol (6 mL) and tetrahydrofuran (12 mL) was added 1 M aqueous sodium hydroxide solution (2.32 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with 1M hydrochloric acid, and diluted with ethyl acetate, and the organic layer was washed with saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/4) to give the title compound (0.52 g, yield 83%) as colorless crystals.

Workup

  1. washthe organic layer was washed with saturated brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-823b593093174c2c9482aed9536e6c21
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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