m-Chloroperbenzoic acid → HCID 178424250, compound

HRID 1617982Notes

Reaction equation

HRID 1617982 reaction equation
[OH:1]/[N:2]=[C:3](/[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([CH3:34])[CH:29]=1)\[CH2:4][C@H:5]([C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].ClC1C=CC=C(C(OO)=[O:43])C=1>ClCCl.CO.C(=O)([O-])O.[Na+].[Cl-].[NH4+]>[C:25]([CH:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:15]=[CH:14][C:13]([C@H:5]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH3:12])[CH2:4]/[C:3](/[C:28]3[CH:33]=[CH:32][N+:31]([O-:43])=[C:30]([CH3:34])[CH:29]=3)=[N:2]\[OH:1])=[CH:18][CH:17]=2)[CH2:24][CH2:23]1)([OH:27])=[O:26]

Participants

7

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136167004HCID 136167004, compound

Product 1

HCID 178424250HCID 178424250, compoundYield 50%

Reagents, catalysts & solvents 4

HCID 25517Ammonium ChlorideCatalystHCID 516892Sodium BicarbonateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (R,E)-1-(4-(3-(hydroxyimino)-3-(2-methylpyridin-4-yl)-1-o-tolylpropyl)-phenyl)piperidine-4-carboxylic acid (example 266; 95 mg, 208 μmol) in dichloromethane (3 mL) and methanol (0.75 mL) was treated with 3-chloroperbenzoic acid (42 mg, 241 μmol) at 0° C. The reaction mixture was allowed to reach room temperature over 3 h, then after addition of sat. aq. sodium hydrogencarbonate solution (3 drops) and sat. aq. ammonium chloride solution (5 drops) concentrated under vacuum. The residue was purified by preparative HPLC to afford the title compound (49 mg, 50%). White foam, MS (ESI+): m/z=474.1 ([M+H]+).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d31fe20eabeb4a39b485df341e050d59
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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