m-Chloroperbenzoic acid → HCID 22866619, compound

HRID 865724Notes

Reaction equation

HRID 865724 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:14]=[C:15]([C@H:20]([CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[CH2:45][CH2:44][CH2:43][NH:42][C:41]3=[O:46])[CH2:36][CH2:35]2)[CH2:21][N:22]([CH3:31])[C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=[CH:17][C:18]=1[Cl:19]>ClCCl>[C:23]([N:22]([CH3:31])[CH2:21][C@H:20]([C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1)[CH2:32][CH2:33][N+:34]1([O-:6])[CH2:35][CH2:36][CH:37]([N:40]2[CH2:45][CH2:44][CH2:43][NH:42][C:41]2=[O:46])[CH2:38][CH2:39]1)(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9871234HCID 9871234, compound

Product 1

HCID 22866619HCID 22866619, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3-Chloroperoxybenzoic acid (0.700 g) in dichloromethane (16 mL) was added dropwise to a solution of (S)-N-[2-(3,4-dichlorophenyl) -4-[4-(2-oxoperhydropyrimidin-1-yl)piperidino]butyl]-N-methylbenzamide (1.31 g) in dichloromethane (12 mL) at 0° C. After being stirred for 1 hour, the reaction mixture was diluted with dichloromethane, washed with aqueous sodium bicarbonate, dried, and evaporated. The crude product was chromatographed, with dichloromethane:methanol (gradient 98:2, 70:30) as eluent. The purified product (0.592 g) and p-toluenesulfonic acid monohydrate (0.232 g) were dissolved in dichloromethane:methanol and evaporated to give the title compound as a white solid (0.824 g); MS: m/z=533(M+1); Analysis for C27H34C12N4O3.1.10 C7H8O3.1.10 H2O: Calculated: C, 56.11; H, 6.10; N, 7.54; Found: C, 55.85; H, 5.96; N, 7.33.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. customdried
  3. customevaporated
  4. customThe crude product was chromatographed, with dichloromethane
  5. dissolutionThe purified product (0.592 g) and p-toluenesulfonic acid monohydrate (0.232 g) were dissolved in dichloromethane
  6. custommethanol and evaporated

Sources & evidence

ORD record
ord-77cdee392bcc410ca14af3961fc46e82
Source dataset
uspto-grants-1996_10
Patent number
US05567700

Reaction notes

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