Sodium periodate → HCID 59627525, compound

HRID 1619903Notes

Reaction equation

HRID 1619903 reaction equation
[OH:1][C:2]1(CO)[CH2:7][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:3]1.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[O:1]=[C:2]1[CH2:7][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:3]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86615516HCID 86615516, compound

Product 1

HCID 59627525HCID 59627525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (223 mg, 0.59 mmol) in tetrahydrofuran (4 mL) was added a solution of sodium periodate (143 mg, 0.67 mmol) in water (1.3 mL) and the mixture stirred for 3 hours. The mixture was concentrated and purified by flash chromatography (silica, gradient 5-20% ethyl acetate in chloroform) to yield tert-butyl [(2R,3S)-5-oxo-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate as white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (silica, gradient 5-20% ethyl acetate in chloroform)

Sources & evidence

ORD record
ord-05621466535b4a54b98dd3dbaf754331
Source dataset
uspto-grants-2014_07
Patent number
US08772328B2

Reaction notes

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