Hydrogen Peroxide → HCID 57431642, compound

HRID 545503Notes

Reaction equation

HRID 545503 reaction equation
C([O-])([O-])=[O:2].[K+].[K+].OO.[C:9]([C:11]1[CH:12]=[C:13]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[C:19]1[CH2:18][CH2:17][CH:16]([NH:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[CH2:15][C:14]2=1)#[N:10]>CS(C)=O.O>[F:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][N:20]1[C:21]2[CH:22]=[CH:23][C:11]([C:9]([NH2:10])=[O:2])=[CH:12][C:13]=2[C:14]2[CH2:15][CH:16]([NH:32][C:33](=[O:37])[CH:34]([CH3:35])[CH3:36])[CH2:17][CH2:18][C:19]1=2

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 11430Potassium CarbonateHCID 57431643HCID 57431643, compound

Product 1

HCID 57431642HCID 57431642, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Add K2CO3 (0.26 g, 1.93 mmol) and 30% H2O2 (2.0 mL) portionwise to N-(6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (Example 51) (1.50 g, 3.85 mmol) in DMSO while cooling in an ice bath. Stir for 18 h and add more H2O2 with warming to 50° C. if needed to facilitate complete reaction. Dilute with water and collect the precipitate by filtration (1.45 g, 92%). Recrystallize from EtOAc to yield a white solid. MS (ES): m/z 408 (M+1); m.p.=192-194° C.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customreaction
  3. customcollect the precipitate
  4. filtrationby filtration (1.45 g, 92%)
  5. customRecrystallize from EtOAc
  6. customto yield a white solid

Sources & evidence

ORD record
ord-11aff49c60cd4dec893597b23d09f446
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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