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Sodium periodate → HCID 86647276, compound

HRID 1695428
Notes
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Reaction equation

HRID 1695428 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 672770305-[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

Product 1

HCID 86647276HCID 86647276, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028
Tetrahydrofuran
Solvent

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

  1. extractionThe reaction mixture was extracted with water and ethyl acetate
  2. washthe organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes