Hydrogen Peroxide → {2-[4-(6-Carbamoylpyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester

HRID 492428Notes

Reaction equation

HRID 492428 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[N:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:27].[K+].[K+].OO>CS(C)=O>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:27])[NH2:24])[N:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 59730328{2-[4-(6-Cyanopyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 59730331{2-[4-(6-Carbamoylpyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl esterYield 158,784,064%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve {2-[4-(6-cyanopyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester (0.814 g, 0.240 mmol) in DMSO (4.8 mL). Add K2CO3 (0.166 g, 0.120 μmol) and then 30% H2O2 (0.071 mL 0.624 mmol). Stir at room temperature for 3 hours. Quench the reaction mixture with water (30 mL). Extract with ethyl acetate (1× 60 mL). Wash the organic layer with water (1× 30 mL), dry over MgSO4, filter and concentrate to give the title compound (68.1 g, 79.5%): MS ES+ 357.9 (M+H)+, base peak ES+ 301.9 (M+2H—C(CH3)3), MS ES− 356.1 (M−H)−; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=18.5 min, 94.5% purity.

Workup

  1. customQuench the reaction mixture with water (30 mL)
  2. extractionExtract with ethyl acetate (1× 60 mL)
  3. washWash the organic layer with water (1× 30 mL)
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-09fe18d4ad7744a1a55421b556307cc9
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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