m-Chloroperbenzoic acid → HCID 57780518, compound

HRID 1095391Notes

Reaction equation

HRID 1095391 reaction equation
[NH2:1][C:2]([C@@H:4]([NH:9][C:10]([N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([CH2:21][CH2:22][S:23]([CH3:25])=[O:24])[C:13]1=[O:26])=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].ClC1C=CC=C(C(OO)=[O:35])C=1.C([O-])(O)=O.[Na+]>ClCCl>[NH2:1][C:2]([C@@H:4]([NH:9][C:10]([N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([CH2:21][CH2:22][S:23]([CH3:25])(=[O:35])=[O:24])[C:13]1=[O:26])=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57780493HCID 57780493, compound

Product 1

HCID 57780518HCID 57780518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[(1S)-1-(aminocarbonyl)-2,2-dimethylpropyl]-3-[2-(methylsulfinyl)ethyl]-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide (Example 33, 150 mg), m-chloroperbenzoic acid (70%, 170 mg) and NaHCO3 (150 mg) in dichloromethane (5 mL) was stirred overnight and quenched with sat. Na2S2O3 aq. (25 mL) The whole was extracted with ethyl acetate (25 mL×2). The combined organic layers were washed with brine, dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was purified by preparative TLC to yield the titled compound. (100 mg)

Workup

  1. customquenched with sat. Na2S2O3 aq. (25 mL) The whole
  2. extractionwas extracted with ethyl acetate (25 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-335d980512e045dfa1706a2ceede277c
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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