m-Chloroperbenzoic acid → HCID 11502978, compound

HRID 2298085Notes

Reaction equation

HRID 2298085 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[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-].[Ca+2].[OH-]>ClCCl>[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:6])=[CH:29][C:14]=1[C:15]([NH:17][CH2:18][C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:27]3)[CH2:26]1)[CH2:28]2)=[O:16]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 10025053HCID 10025053, compound

Product 1

HCID 11502978HCID 11502978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperoxybenzoic acid (166 mg) was added to a solution of 2-chloro-5-(piperidin-4-ylsulfanyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.35 g, Example 55c) in dichloromethane (5 ml). After 2 h calcium hydroxide (0.20 g) was added and 30 min. later the salts removed by filtration. The filtrate was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (eluting with 0-25% ethanol in dichloromethane). The residue was dissolved in methanol (5 ml) and hydrochloric acid (0.5 ml of a 4N solution in dioxane) was added. After stirring at room temperature for 14 h, the solution was concentrated under reduced pressure and triturated with diethyl ether to yield the title compound as the hydrochloride salt (0.030 g).

Workup

  1. customremoved by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give a residue which
  4. customwas purified by silica gel chromatography (eluting with 0-25% ethanol in dichloromethane)
  5. dissolutionThe residue was dissolved in methanol (5 ml)
  6. additionhydrochloric acid (0.5 ml of a 4N solution in dioxane) was added
  7. concentrationthe solution was concentrated under reduced pressure
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-5f8c7745965c463b8d0e5a7cd0ea833d
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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