Sodium periodate → HCID 60026395, compound

HRID 400684Notes

Reaction equation

HRID 400684 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([CH2:19][C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([S:29][CH3:30])=[CH:24][CH:23]=2)([OH:18])[CH2:4][C:5]([C:8]1[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=[C:10]([F:17])[CH:9]=1)([CH3:7])[CH3:6].I([O-])(=O)(=O)=[O:34].[Na+]>CO.[Cl-].[Na+].O>[F:32][C:2]([F:1])([F:31])[C:3]([CH2:19][C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][C:25]([S:29]([CH3:30])=[O:34])=[CH:24][CH:23]=2)([OH:18])[CH2:4][C:5]([C:8]1[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=[C:10]([F:17])[CH:9]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 60026509HCID 60026509, compound

Product 1

HCID 60026395HCID 60026395, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(5-methylsulfanyl-1H-indol-2-ylmethyl)pentan-2-ol (25 mg, 0.053 mmol) in 10 mL of methanol was added sodium periodate (150 mg, 0.70 mmol). After 1 hour, the mixture was diluted with brine and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by preparative TLC on silica gel eluting with ethyl acetate to afford 19.8 mg (77% yield) of the title compound.

Workup

  1. extractionextracted with three 10 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with three 7 mL portions of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative TLC on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-193cf8200d844d6c96143a2a51fe5460
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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