2-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy)-3-pyridyl]acetic acid → Sodium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetate

HRID 1294356Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

1N Sodium hydroxide-methanol solution (2.4 ml) was added to 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid (1.0 g) and the mixture was heated to 40° C. The obtained solution was allowed to cool and acetone (10 ml) was added. The mixture was stirred at room temperature for 30 min and acetone (5 ml) was further added. The mixture was stirred at room temperature for 1 hr, and under ice-cooling for 1 hr. The precipitated crystals were collected by filtration, washed with acetone (10 ml) ice-cooled in advance, and dried under reduced pressure to give sodium 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetate as white crystals.

Workup

temperatureto cool
stirringThe mixture was stirred at room temperature for 1 hr
temperatureunder ice-cooling for 1 hr
filtrationThe precipitated crystals were collected by filtration
washwashed with acetone (10 ml) ice-
temperaturecooled in advance
customdried under reduced pressure

Sources & evidence

ORD record: ord-cd26b81ae12940f498b96783a335b2b0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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