Hydrogen Peroxide → (R)-tert-butyl 1-(4-carbamoyl-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate

HRID 84845Notes

Reaction equation

HRID 84845 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C@@H:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][O:13][CH3:14])=[CH:5][C:4]=1[NH:23][C:24]1[S:28][N:27]=[C:26]([CH3:29])[CH:25]=1)#[N:2].C([O-])([O-])=[O:31].[K+].[K+].OO>CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C@@H:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH2:12][O:13][CH3:14])=[CH:5][C:4]=1[NH:23][C:24]1[S:28][N:27]=[C:26]([CH3:29])[CH:25]=1)(=[O:31])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67773713HCID 67773713, compound

Product 1

HCID 67515833(R)-tert-butyl 1-(4-carbamoyl-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The above mentioned crude oil from step 2 was dissolved in DMSO (2 mL), K2CO3 (500 mg, 3.6 mmol) was added; then H2O2 (50% aq., 2 mL) was added dropwise (gas evolved). The mixture was stirred at 80° C. for 15 min, cooled and was diluted with water, the resulting precipitate was collected by filtration, dried in vacuo to give (R)-tert-butyl 1-(4-carbamoyl-3-(3-methylisothiazol-5-ylamino)phenylamino)-3-methoxypropan-2-ylcarbamate as solid.

Workup

  1. temperaturecooled
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b0b9b8e2b2fb4c38b813825d5c2962f1
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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