m-Chloroperbenzoic acid → (+/-)-2-Chloro-5-[2-(3-hydroxypropylsulfinyl)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085647Notes

Reaction equation

HRID 2085647 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].ClC1C=C(C=CC=1)C(OO)=[O:35]>>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][S:25]([CH2:26][CH2:27][CH2:28][OH:29])=[O:35])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2)=[O:5]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 101815962-Chloro-5-[2-(3-hydroxypropylthio)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 10204466(+/-)-2-Chloro-5-[2-(3-hydroxypropylsulfinyl)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 56.3%

Procedure

Prepared according to the method of Example 14 using 2-chloro-5-[2-(3-hydroxypropylthio)ethoxy]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 15, 0.12 g) and 3-chloroperoxybenzoic acid (0.07 g, 70%) to give the title compound (0.07 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ebb99ab15d514d9c82a84ae820570529
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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