m-Chloroperbenzoic acid → HCID 178427149, compound

HRID 1629847Notes

Reaction equation

HRID 1629847 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]([C@@H:9]([NH:11][C:12](=[O:27])[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][S:22][CH2:21][C:20]4=[O:25])=[C:15]([CH3:26])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:38])C=1.C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]([C@@H:9]([NH:11][C:12](=[O:27])[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][S:22](=[O:38])[CH2:21][C:20]4=[O:25])=[C:15]([CH3:26])[CH:14]=3)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178427148HCID 178427148, compound

Product 1

HCID 178427149HCID 178427149, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-12.5 °C

Procedure

204 mg (0.48 mmol) N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethyl]-3-methyl-4-(thiomorpholin-3-on-4-yl)-benzamide are dissolved in a mixture of 12 ml dichloromethane and 1.2 ml acetic acid at −15° C. and combined with 110 mg (0.48 mmol) 3-chloroperbenzoic acid. The mixture is then stirred for one hour at −15 to −10° C., heated to ambient temperature and stirred for a further 3 hours. Then the reaction mixture is combined with semi-concentrated sodium hydrogen carbonate solution and extracted with a solvent mixture dichloromethane/methanol 19:1. The combined organic phases are washed with water, dried over magnesium sulphate, evaporated down i. vac. and purified by chromatography on silica gel (eluting gradient: ethyl acetate/(ethanol/conc. ammonia solution 19:1)=1:0->4:1).

Workup

  1. temperatureheated to ambient temperature
  2. stirringstirred for a further 3 hours
  3. extractionextracted with a solvent mixture dichloromethane/methanol 19:1
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated down i
  7. customand purified by chromatography on silica gel (eluting gradient: ethyl acetate/(ethanol/conc. ammonia solution 19:1)=1:0->4:1)

Sources & evidence

ORD record
ord-e38f4e1da9c7412c9e4d44b544d62220
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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