Hydrogen Peroxide → HCID 86689953, compound

HRID 1626941Notes

Reaction equation

HRID 1626941 reaction equation
[C:1](=[O:38])([O:3][C:4]([CH3:37])([CH3:36])[CH2:5][C@@H:6]([CH2:17][C:18]([N:21]1[CH2:25][CH2:24][C@H:23]2[CH2:26][N:27]([C:29]([C:31]3([C:34]#[N:35])[CH2:33][CH2:32]3)=[O:30])[CH2:28][C@@H:22]12)=[C:19]=[O:20])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])[NH2:2].OO.C(=O)([O-])[O-:42].[K+].[K+].O>CS(C)=O>[C:1](=[O:38])([O:3][C:4]([CH3:36])([CH3:37])[CH2:5][C@@H:6]([CH2:17][C:18]([N:21]1[CH2:25][CH2:24][C@H:23]2[CH2:26][N:27]([C:29]([C:31]3([C:34]([NH2:35])=[O:42])[CH2:32][CH2:33]3)=[O:30])[CH2:28][C@@H:22]12)=[C:19]=[O:20])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[F:16])[NH2:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 86689954HCID 86689954, compound

Product 1

HCID 86689953HCID 86689953, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(R)-4-((3aS,6aS)-5-(1-cyanocyclopropylcarbonyl)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-4-carbonyl-1-(2,4,5-trifluorophenyl)butan-2-yltertbutyl carbamate 17a (300 mg, 0.58 mmol) was dissolved in DMSO (5 mL), added 30% of hydrogen peroxide (0.5 mL) and potassium carbonate (160 mg, 1.16 mmol) at 0° C., the temperature of reaction solution was raised to room temperature and stirred for 5 minutes, added water (20 mL), extracted by dichloromethane, dried by anhydrous sodium sulfate, concentrated, residues was purified by column chromatography to give (R)-4-((3aS,6aS)-5-(1-aminocarbonylcyclopropylcarbonyl)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-4-carbonyl-1-(2,4,5-trifluorophenyl)butan-2-yltertbutyl carbamate 28a (265 mg, 85%) as white foamy solid. MS m/z (ESI): 539.2 (M+1).

Workup

  1. customthe temperature of reaction solution
  2. extractionextracted by dichloromethane
  3. dry with materialdried by anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customresidues was purified by column chromatography

Sources & evidence

ORD record
ord-808ee65ca9d340fe84aae7e422f55809
Source dataset
uspto-grants-2014_07
Patent number
US08785477B2

Reaction notes

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