Hydrogen Peroxide → HCID 57937843, compound

HRID 1435069Notes

Reaction equation

HRID 1435069 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=2)=[C:16]([F:28])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:31].[K+].[K+].OO>CS(C)=O.O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=[O:31])[NH2:27])[CH:21]=2)=[C:16]([F:28])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 57937830HCID 57937830, compound

Product 1

HCID 57937843HCID 57937843, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(3′-Cyano-2-fluoro-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-5d: 1.20 g, 3.02 mmol) was dissolved in dimethyl sulfoxide (5.5 ml) and treated with potassium carbonate (0.502 g, 3.6 mmol) and 0.250 ml of a 30% hydrogen peroxide solution. After 18 hours, the reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (1.25 g, 99%), which was pure enough to be taken on and used directly in the next reaction.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b536a58eb49b40b7b18dc0f987be23cb
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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