m-Chloroperbenzoic acid → 2-Chloro-5-[3-(3-hydroxypropylsulfonyl)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085642Notes

Reaction equation

HRID 2085642 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][S:37][CH2:38][CH2:39][CH2:40][OH:41])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:16].[OH-:42].[Ca+2].[OH-:44]>ClCCl>[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][S:37]([CH2:38][CH2:39][CH2:40][OH:41])(=[O:44])=[O:42])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:20][CH:21]3[CH2:27][CH:25]([CH2:24][CH:23]([CH2:22]3)[CH2:28]1)[CH2:26]2)=[O:16]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 102259552-Chloro-5-[3-(3-hydroxypropylthio)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 227314902-Chloro-5-[3-(3-hydroxypropylsulfonyl)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (0.14 g, 70%) was added to a solution of 2-chloro-5-[3-(3-hydroxypropylthio)propoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 10, 0.1 g) in dichloromethane (10 ml). After 1 hour calcium hydroxide (0.1 g) was added and stirring continued for a further 30 min. The reaction mixture was dried (MgSO4), filtered through celite and concentrated. The residue was triturated with ethanol to leave the title compound as a white solid (0.030 g).

Workup

  1. dry with materialThe reaction mixture was dried (MgSO4)
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe residue was triturated with ethanol

Sources & evidence

ORD record
ord-4be6368b7f4c4b4d9a7e57dae3e5a769
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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