Hydrogen Peroxide → HCID 178429011, compound

HRID 1913562Notes

Reaction equation

HRID 1913562 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]([C:19](=[O:43])[N:20]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]#[N:42])[CH:36]=1)[CH:21]([C:23]1[NH:24][CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:27]=1)[CH3:22])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[CH:12][C:11]=1[CH3:18])([CH3:4])([CH3:3])[CH3:2].[OH:45]O.[OH-].[Na+]>CCO>[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]([C:19](=[O:43])[N:20]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41](=[O:45])[NH2:42])[CH:36]=1)[CH:21]([C:23]1[NH:24][CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:27]=1)[CH3:22])[CH2:9][C:10]1[C:11]([CH3:18])=[CH:12][C:13]([OH:17])=[CH:14][C:15]=1[CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178429010HCID 178429010, compound

Product 1

HCID 178429011HCID 178429011, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
7.5 °C

Procedure

A solution of [1-{(3-cyano-benzyl)-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamoyl}-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (0.070 g, 0.12 mmol) in 3 mL of EtOH was treated with 1.0 mL of 30% hydrogen peroxide followed immediately by 0.1 mL of a 6M aqueous solution of NaOH. The reaction mixture was stirred vigorously for 18 h and quenched by pouring into chilled (5-10° C.) water. The aqueous solution was extracted five times with Et2O and the combined extracts were dried over MgSO4, filtered, and concentrated to provide 0.051 g of [1-{(3-carbamoyl-benzyl)-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamoyl}-2-(4-hydroxy-2,6-dimethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester as a colorless residue (HPLC: 84% @ 254 nm and 77% @ 214 nm). MS (ES+) (relative intensity): 612.5 (100) (M+1). This sample was of sufficient quality to use in the next reaction without further purification.

Workup

  1. customquenched
  2. additionby pouring
  3. extractionThe aqueous solution was extracted five times with Et2O
  4. dry with materialthe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-17be3441d1304897a792c928a953c1ff
Source dataset
uspto-grants-2013_12
Patent number
US08609709B2

Reaction notes

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