m-Chloroperbenzoic acid → HCID 21201668, compound

HRID 1979309Notes

Reaction equation

HRID 1979309 reaction equation
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([S:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=2)=[O:27])[C:9]1=[O:42])=[O:6])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:51])C=1>C(Cl)Cl>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([S:35]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:51])[CH:30]=2)=[O:27])[C:9]1=[O:42])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21201669HCID 21201669, compound

Product 1

HCID 21201668HCID 21201668, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1-tert-Butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-ethoxycarbonylmethylthiophenyl)urea (460 mg) obtained from Step 2 of Example 33 was dissolved in methylene chloride (20 ml), m-chloroperbenzoic acid (170mg) was added under ice-cooling, stirred for 30 minutes. The reaction mixture was washed subsequently with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodiun sulfate, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2), to thereby obtain 320 mg of the title compound (Yield: 68%).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed subsequently with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous sodiun sulfate
  4. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-2dd8d587f3154dc1ba54f77b4d35c594
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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