Hydrogen Peroxide → HCID 10163613, compound

HRID 892330Notes

Reaction equation

HRID 892330 reaction equation
ON[C:3](=[NH:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:14]3[C:15](=[O:32])[N:16]([C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]5=[O:31])=[CH:21][CH:20]=4)[CH2:17][CH2:18][C:13]=3[C:12]([C:33]([F:36])([F:35])[F:34])=[N:11]2)[CH:5]=1.[OH-:38].[Na+].OO>ClCCl>[O:32]=[C:15]1[C:14]2[N:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([NH2:37])=[O:38])[N:11]=[C:12]([C:33]([F:34])([F:36])[F:35])[C:13]=2[CH2:18][CH2:17][N:16]1[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]2=[O:31])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178513309HCID 178513309, compound

Product 1

HCID 10163613HCID 10163613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 116, part A (0.05 g) was dissolved in dichloromethane (10 mL). To this was added sodium hydroxide (1N, 5 mL), hydrogen peroxide (3 mL), and tetrabutylammonium-hydroxide (0.01 g). The reaction mixture was stirred at rt for 24 h and concentrated. Quenched with water (50 mL) and the organics extracted with ethylacetate (2×50 mL), dried (MgSO4) and concentrated. The crude was purified via prep HPLC to a colorless solid. ESI mass spectrum 494(M+H) and 492(M−H).

Workup

  1. concentrationconcentrated
  2. customQuenched with water (50 mL)
  3. extractionthe organics extracted with ethylacetate (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude was purified via prep HPLC to a colorless solid

Sources & evidence

ORD record
ord-1257d06db9e84c61981c196211f7f9fb
Source dataset
uspto-grants-2006_02
Patent number
US07005435B2

Reaction notes

Loading…