Hydrogen Peroxide → HCID 67126953, compound

HRID 706887Notes

Reaction equation

HRID 706887 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:31]=[C:30]([N:32]4[CH2:37][CH2:36][N:35]([CH2:38][C:39]5[CH2:44][CH2:43][C:42]([CH3:46])([CH3:45])[CH2:41][C:40]=5[C:47]5[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=5)[CH2:34][CH2:33]4)[CH:29]=[CH:28][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([C:26]#[N:27])[CH:20]=3)(=[O:18])=[O:17])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[O:54]1CCCC1.OO.[OH-].[Na+]>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:31]=[C:30]([N:32]4[CH2:33][CH2:34][N:35]([CH2:38][C:39]5[CH2:44][CH2:43][C:42]([CH3:46])([CH3:45])[CH2:41][C:40]=5[C:47]5[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=5)[CH2:36][CH2:37]4)[CH:29]=[CH:28][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([C:26](=[O:54])[NH2:27])[CH:20]=3)(=[O:17])=[O:18])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 67127200HCID 67127200, compound

Product 1

HCID 67126953HCID 67126953, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of EXAMPLE 70B (90 mg) in ethanol (2 mL) was added tetrahydrofuran (2 mL), hydrogen peroxide (30%, 1 mL) and 1M sodium hydroxide solution (0.48 mL), followed by an additional 2 mL of tetrahydrofuran. The reaction was heated to 45° C. for 30 minutes, cooled, and then quenched with 5% HCl solution and extracted twice with dichloromethane. The extracts were combined and concentrated to obtain the product.

Workup

  1. temperaturecooled
  2. customquenched with 5% HCl solution
  3. extractionextracted twice with dichloromethane
  4. concentrationconcentrated
  5. customto obtain the product

Sources & evidence

ORD record
ord-1dbb172e9176468c90e6e35e7a6d1d34
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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