Sodium Thiosulfate → HCID 46202115, compound

HRID 1192729Notes

Reaction equation

HRID 1192729 reaction equation
[CH:1]1([CH2:4][C:5]([F:36])([F:35])[CH2:6][C@H:7]([NH:22][CH2:23][C:24]([F:34])([F:33])[O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:8]([NH:10][C@@H:11]([CH2:20][CH3:21])[CH:12]([OH:19])[C:13]([NH:15][CH:16]2[CH2:18][CH2:17]2)=[O:14])=[O:9])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN1CCCC1>[CH:1]1([CH2:4][C:5]([F:36])([F:35])[CH2:6][C@H:7]([NH:22][CH2:23][C:24]([F:33])([F:34])[O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:8]([NH:10][C@@H:11]([CH2:20][CH3:21])[C:12](=[O:19])[C:13]([NH:15][CH:16]2[CH2:17][CH2:18]2)=[O:14])=[O:9])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67378535HCID 67378535, compound

Product 1

HCID 46202115HCID 46202115, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

To a solution of (2S)-5-cyclopropyl-N-((3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-yl)-2-(2,2-difluoro-2-(4-fluorophenoxy)ethylamino)-4,4-difluoropentanamide (190 mg, 0.36 mmol) in N-methylpyrrolidine (4 ml) was added Dess-Martin periodinane reagent (216 mg, 0.51 mmol, 1.4 eq). The mixture was stirred for 4 hours at room temperature, then added to saturated aqueous sodium bicarbonate (50 ml) containing sodium thiosulfate (1.5 g). The mixture was stirred for 1 hour, filtered, the solid material washed with water, then dried in a vacuum oven at 40° C. using phosphorus pentoxide as a drying agent, yielding (S)-5-cyclopropyl-N-((S)-1-(cyclopropylamino)-1,2-dioxopentan-3-yl)-2-(2,2-difluoro-2-(4-fluorophenoxy)ethylamino)-4,4-difluoropentanamide 144 mg (76%).

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. filtrationfiltered
  3. washthe solid material washed with water
  4. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-e6a82a5845be46fbbb8068016a2bf9c0
Source dataset
uspto-grants-2014_03
Patent number
US08680152B2

Reaction notes

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