Sodium periodate → HCID 86647276, compound

HRID 1695428Notes

Reaction equation

[O-]I(=O)(=O)=O.[Na+].[CH3:7][O:8][C:9]([C:11]1[N:12]([CH3:40])[N:13]=[C:14]([O:16][CH2:17][C:18]2[C:19]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[N:20][O:21][C:22]=2[C@@H:23]([OH:32])[C@H](O)C2C=CC=CC=2)[CH:15]=1)=[O:10]>C1COCC1.O>[CH3:7][O:8][C:9]([C:11]1[N:12]([CH3:40])[N:13]=[C:14]([O:16][CH2:17][C:18]2[C:19]([C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[N:20][O:21][C:22]=2[CH:23]=[O:32])[CH:15]=1)=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium (meta)periodate (3.67 g, 17.2 mmol) was added at 0° C. to a mixture of 5-[5-((1S,2R)-1,2-dihydroxy-2-phenyl-ethyl)-3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (5.35 g, 11.4 mmol) in THF (29.6 ml) and water (6.1 ml) and the resulting mixture stirred at 0° C. over night. The reaction mixture was extracted with water and ethyl acetate, and the organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:0 to 4:1) afforded the title compound (3.63 g, 88%) as a white solid. MS: m/e=418.1 [M+OAc]−.

Workup

extractionThe reaction mixture was extracted with water and ethyl acetate
washthe organic phases were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customPurification by chromatography (silica, heptane:ethyl acetate=1:0 to 4:1)

Sources & evidence

ORD record: ord-a991146a64114db9aca5d3c82af7bacb
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

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