m-Chloroperbenzoic acid → HCID 57780493, compound

HRID 1095390Notes

Reaction equation

HRID 1095390 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][CH3:24])[C:13]1=[O:25])=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].ClC1C=CC=C(C(OO)=[O:34])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]([CH3:24])=[O:34])[C:13]1=[O:25])=[O:11])[C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57780514HCID 57780514, compound

Product 1

HCID 57780493HCID 57780493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[(1S)-1-(aminocarbonyl)-2,2-dimethylpropyl]-3-[2-(methylthio)ethyl]-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide (Example 32, 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. (180 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-7d5ae5c62bf947559e137ee37d340ba9
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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