Hydrogen Peroxide → tert-butyl (1S,2R)-2-(5-carbamoyl-3-fluoro-6-(3-methylisoxazol-5-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

HRID 84915Notes

Reaction equation

HRID 84915 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([F:31])[C:6]([NH:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:7][C:8]=1[NH:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1)#[N:2].[OH-:32].[Na+].OO.O>CCO.CS(C)=O.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([F:31])[C:6]([NH:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[N:7][C:8]=1[NH:9][C:10]1[O:14][N:13]=[C:12]([CH3:15])[CH:11]=1)(=[O:32])[NH2:2]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 68078498tert-butyl (1S,2R)-2-(5-cyano-3-fluoro-6-(3-methylisoxazol-5-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

Product 1

HCID 68077619tert-butyl (1S,2R)-2-(5-carbamoyl-3-fluoro-6-(3-methylisoxazol-5-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the crude tert-butyl (1S,2R)-2-(5-cyano-3-fluoro-6-(3-methylisoxazol-5-ylamino)pyridin-2-ylamino)cyclohexylcarbamate in EtOH (2 mL) and DMSO (2 mL), aq. 1N NaOH (1 mL) and aq. H2O2 (50%, 1 mL) were added. The mixture was stirred at room temperature for 15 min. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give crude tert-butyl (1S,2R)-2-(5-carbamoyl-3-fluoro-6-(3-methylisoxazol-5-ylamino)pyridin-2-ylamino)cyclohexylcarbamate, which was then dissolved in TFA (4 mL). After 10 min, excess TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (18 mg). MS 349.3 (M+H); UV 201.0, 259.0, 295.8, 333.5 nm; t 0.450 min.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-301e1cb3bb14446c9d988083a1104b86
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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