Hydrochloric Acid → HCID 68884627, compound

HRID 1294345Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:35]=[CH:34][C:22]([CH2:23][O:24][C:25]2[C:30]([CH2:31][C:32]#N)=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:21][CH:20]=1.[OH-:36].[Na+].C(O)C.Cl.[OH2:42]>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][O:24][C:25]2[C:30]([CH2:31][C:32]([OH:42])=[O:36])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:34][CH:35]=1

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 962Water

HCID 14798Sodium Hydroxide

HCID 68883837HCID 68883837, compound

Product 1

HCID 68884627HCID 68884627, compoundYield 58%

Procedure

A mixture of 2-[2-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyloxy]-3-pyridyl]acetonitrile (700 mg), a 2N aqueous sodium hydroxide solution (20 mL) and ethanol (40 mL) was heated under reflux for 18 hours. Water was added to the reaction mixture, and the mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (420 mg, 58%) of 2-[2-[4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyloxy]-3-pyridyl]acetic acid from a fraction eluted with acetone-hexane (2:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 155-156° C.

Workup

temperatureunder reflux for 18 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-8d39745f3de94690a5c090d845b88a68
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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