Metaperiodic acid → HCID 86590547, compound

HRID 1880530Notes

Reaction equation

HRID 1880530 reaction equation
I(O)(=O)(=O)=[O:2].[F:6][C:7]([F:36])([F:35])[CH2:8][CH2:9][C@H:10]([NH:13][C@@H:14]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:15]([F:18])([F:17])[F:16])[CH2:11][OH:12]>C(#N)C.[O-2].[O-2].[O-2].[Cr+6]>[F:36][C:7]([F:6])([F:35])[CH2:8][CH2:9][C@H:10]([NH:13][C@@H:14]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:15]([F:16])([F:17])[F:18])[C:11]([OH:2])=[O:12]

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 86590548(2S)-5,5,5-trifluoro-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)-1,1'-biphenyl-4-yl]ethyl}amino)pentan-1-ol

Product 1

HCID 86590547HCID 86590547, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A stock oxidant suspension was prepared by stirring periodic acid (2.28 g) and chromium trioxide (4.6 mg) in wet acetonitrile (0.75% water) to create a suspension of total volume of 22.8 mL. The oxidant suspension (4.22 mL) was then added to a stirred solution of (2S)-5,5,5-trifluoro-2-({(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)-1,1′-biphenyl-4-yl]ethyl}amino)pentan-1-ol (0.35 g, 0.74 mmol) in wet acetonitrile (3.7 mL) dropwise while maintaining the temperature at 0-5° C. The reaction mixture was allowed to warm to ambient temperature after one hour and then stirred for an additional 4 hours. The reaction was quenched with aqueous sodium hydrogen phosphate (6 g/100 mL) and toluene was added and the mixture shaken vigorously. The organic phase was washed with 1:1 brine:water, then with aqueous sodium bisulfite (2.2 g/50 mL), then brine. The organic layer was then dried with sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by silica gel chromatography using 5-10% methanol in methylene chloride as eluant to yield (2S)-5,5,5-trifluoro-2-({(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)-1,1′-biphenyl-4-yl]ethyl}amino)pentanoic acid.

Workup

  1. customA stock oxidant suspension was prepared
  2. additiona suspension of total volume of 22.8 mL
  3. temperatureto warm to ambient temperature after one hour
  4. customThe reaction was quenched with aqueous sodium hydrogen phosphate (6 g/100 mL) and toluene
  5. additionwas added
  6. stirringthe mixture shaken vigorously
  7. washThe organic phase was washed with 1:1 brine
  8. dry with materialThe organic layer was then dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation
  11. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-284e2191ff9d4e6997235b7378439499
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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