Hydrogen Peroxide → (R)-4-(1-amino-3-(benzyloxy)-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 2201052

Reaction equation

HRID 2201052 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[CH:25]=2)[CH:16]=1)[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=[O:31].[K+].[K+].OO>CS(C)=O>[NH2:13][C:11](=[O:12])[C@H:10]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH2:22])=[O:31])=[C:17]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[CH:25]=2)[CH:16]=1)[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67508575(R)-3-(benzyloxy)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide

Product 1

HCID 57334483(R)-4-(1-amino-3-(benzyloxy)-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamideYield 7.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (R)-3-(benzyloxy)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (73 mg, 0.18 mmol) in DMSO (2 mL), K2CO3 (200 mg, 1.44 mmol) and H2O2 (50% aq., 1.00 mL) were added. After being stirred at 90 C for 15 min, the mixture was purified by HPLC to give the titled compound (6 mg). MS 426.3 (M+H); UV 200.4, 293.4 nm

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-76d340030ca6436bac1fa3286733bffe
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Linked notes

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