Sodium periodate → HCID 86644370, compound

HRID 1920945Notes

Reaction equation

HRID 1920945 reaction equation
[O-]I(=O)(=O)=O.[Na+].[CH3:7][O:8][C:9]([C:11]1[O:15][N:14]=[C:13]([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:12]=1)=[O:10]>C1COCC1.O>[CH3:7][O:8][C:9]([C:11]1[O:15][N:14]=[C:13]([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:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 67491984HCID 67491984, compound

Product 1

HCID 86644370HCID 86644370, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium (meta)periodate (2.68 g, 8.4 mmol) was added to a solution of 3-[5-((1S,2R)-1,2-dihydroxy-2-phenyl-ethyl)-3-(4-fluoro-phenyl)-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester (3.8 g, 8.4 mmol) in THF (21 mL) and de-ionized water (4.3 mL) at 0° C. and the resulting mixture stirred overnight at 0° C. The reaction mixture was extracted with ethyl acetate the combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated to afford the title compound (2.9 g, 100%) which was obtained as a colorless oil and used in the next step directly. MS: m/e=405.1 [M+OAc]−.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate the combined organic phases
  2. washwere washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f9bce829d15844c38e605f7ff89a205e
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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