Chlorine → HCID 178453652, compound

HRID 2053837Notes

Reaction equation

HRID 2053837 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]2[NH:6][C:7]([C@@H:9]([NH:15][C:16](=[O:40])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][C@H:26]4[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:24])=[C:19]([Cl:39])[CH:18]=3)[CH2:10][CH2:11][S:12]([CH3:14])=[O:13])=[N:8][C:4]=2[CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:48].ClCCl.CO.ClCl>ClCCl>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]2[NH:6][C:7]([C@@H:9]([NH:15][C:16](=[O:40])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][CH2:28][CH2:27][C@H:26]4[CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:24])=[C:19]([Cl:39])[CH:18]=3)[CH2:10][CH2:11][S:12]([CH3:14])(=[O:48])=[O:13])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 24526ChlorineHCID 70297m-Chloroperbenzoic acidHCID 21226129Dichloromethane methanolHCID 178504636HCID 178504636, compound

Product 1

HCID 178453652HCID 178453652, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared analogously to Example 85 from N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfinylpropyl]-3-chloro-4-[(2S)-2-(N-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]benzamide and 2 equivalents of 3-chloroperoxybenzoic acid in dichloromethane/glacial acetic acid. Yield: 46%; Rf value: 0.38 (silica gel; dichloromethane/methanol=9:1); C29H35Cl2N5O6S (652.60); mass spectrum: (M+H)+=652/654/656 (chlorine isotope).

Sources & evidence

ORD record
ord-a686660a4d9e4cf6bb5052dd095de5e9
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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