Sodium Hydroxide → (5-Methyl-2-pyridin-3-yl-1,3-oxazol-4-yl)acetic acid

HRID 2211978Notes

Reaction equation

[OH-].[Li+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]=1[CH2:15][C:16]([OH:18])=[O:17].[OH-].[Na+]>C(O)C>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]=1[CH2:15][C:16]([OH:18])=[O:17]

Participants

Conditions

Temperature: 22 °C

Procedure

(5-Methyl-2-pyridin-3-yl-1,3-oxazol4-yl)acetic acid lithium hydroxide (12 mg) added. The mixture was stirred at 22° C. for 17 h and heated at 60° C. for 2 h. Ethanol (3 ml) and 2N aqueous sodium hydroxide (1 ml) were added, and stirring was continued at 22° C. for 2 h. The mixture was applied to a sulphonic acid ion exchange cartridge (10 g Isolute SCX) and eluted with methanol followed by 10% triethylamine in methanol. Evaporation of the triethylamine containing fraction gave the title compound as a gum (46 mg).

Workup

temperatureheated at 60° C. for 2 h
stirringstirring
waitwas continued at 22° C. for 2 h
washeluted with methanol
customEvaporation of the triethylamine containing fraction

Sources & evidence

ORD record: ord-a7f46ab882a34366a3bd8509dbe0b5b8
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101882B2

Reaction notes

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