Hydrogen Peroxide → HCID 86706450, compound

HRID 919570Notes

Reaction equation

HRID 919570 reaction equation
[O:1]=[CH:2][CH2:3][N:4]([C:18]1[C:19]2[CH:26]=[CH:25][N:24]([S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:20]=2[N:21]=[CH:22][N:23]=1)[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.[OH:37]O>CC#N.CCOC(C)=O>[C:14]([O:13][C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@@H:5]([N:4]([C:18]2[C:19]3[CH:26]=[CH:25][N:24]([S:27]([C:30]4[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=4)(=[O:28])=[O:29])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:3][C:2]([OH:37])=[O:1])[CH2:6]1)=[O:12])([CH3:16])([CH3:17])[CH3:15]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 86706451HCID 86706451, compound

Product 1

HCID 86706450HCID 86706450, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-tert-butyl 3-((2-oxoethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (0.5 g, 0.97 mmol) in CH3CN (2 mL) at rt, was added an aq. solution of NaH2PO4 (3 mL, 0.21 g, 1.75 mmol), aq. NaO2Cl (2 mL, 0.16 g, 1.75 mmol) and 30% H2O2 (0.17 ml, 1.5 mmol) at 0° C. The reaction mixture was warmed to rt and stirred for overnight. The organic phase was concentrated in vacuo to afford a residue that was dissolved in EtOAc, filtered and dried over Na2SO4, concentrated in vacuo and purified by column chromatography (Silica gel, gradient MeOH: CH2Cl2) to afford the titled compound (0.105 g, 20.38%). LCMS [M+1]: 530.

Workup

  1. concentrationThe organic phase was concentrated in vacuo
  2. customto afford a residue that
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (Silica gel, gradient MeOH: CH2Cl2)

Sources & evidence

ORD record
ord-90b14104737e4dc6b2bc94328db9f90c
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…