m-Chloroperbenzoic acid → HCID 178504636, compound

HRID 2053836Notes

Reaction equation

HRID 2053836 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:52]=[CH:51][C:16]2[NH:17][C:18]([C@@H:20]([NH:25][C:26](=[O:50])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([N:35]4[CH2:39][CH2:38][CH2:37][C@H:36]4[CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:34])=[C:29]([Cl:49])[CH:28]=3)[CH2:21][CH2:22][S:23][CH3:24])=[N:19][C:15]=2[CH:14]=1>ClCCl.C(O)(=O)C>[Cl:12][C:13]1[CH:52]=[CH:51][C:16]2[NH:17][C:18]([C@@H:20]([NH:25][C:26](=[O:50])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([N:35]4[CH2:39][CH2:38][CH2:37][C@H:36]4[CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:34])=[C:29]([Cl:49])[CH:28]=3)[CH2:21][CH2:22][S:23]([CH3:24])=[O:6])=[N:19][C:15]=2[CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178503699HCID 178503699, compound

Product 1

HCID 178504636HCID 178504636, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

0.1 g (0.4 mmol) of 3-chloroperoxybenzoic acid is added at −10° C. to a solution of 0.3 g (0.4 mmol) of N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropyl]-3-chloro-4-[(2S)-2-(N-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]benzamide in 10 mL of dichloromethane and 1 mL of glacial acetic acid and stirred for 30 minutes. Then the mixture is stirred for 4 hours at ambient temperature and washed with 5% sodium carbonate solution. The combined organic phases are dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel, eluting with dichloromethane/methanol (0%-10%). Yield: 0.1 g (59%); Rf value: 0.42 (silica gel; dichloromethane/methanol=9:1); C29H35Cl2N5O5S (636.60); mass spectrum: (M+H)+=636/638/640 (chlorine isotope) and (M−H)−=634/636/638 (chlorine isotope).

Workup

  1. stirringThen the mixture is stirred for 4 hours at ambient temperature
  2. washwashed with 5% sodium carbonate solution
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel
  6. washeluting with dichloromethane/methanol (0%-10%)

Sources & evidence

ORD record
ord-988ed005396343b6b818bb1222f81fea
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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