m-Chloroperbenzoic acid → HCID 131723693, compound

HRID 2298088Notes

Reaction equation

HRID 2298088 reaction equation
[Cl:1]C1C=C(C=CC=1)C(OO)=O.[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33][CH2:34][C:35]2(C(OC(C)(C)C)=O)[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]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-:48].[Ca+2].[OH-:50]>C(Cl)(Cl)Cl>[ClH:1].[Cl:12][C:13]1[CH:32]=[CH:31][C:30]([S:33]([CH2:34][CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)(=[O:50])=[O:48])=[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]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 18381557HCID 18381557, compound

Product 1

HCID 131723693HCID 131723693, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

m-Chloroperoxybenzoic acid (0.19 g) was added to a solution 2-chloro-5-(4-[{1,1-dimethylethyl}oxycarbonyl]piperidin-4-ylmethylsulfanyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.165 g, Example 58a) in chloroform (10 ml). After 5 h calcium hydroxide (120 mg) was added and 30 min. later the salts removed by filtration. The reaction mixture was concentrated, then dissolved in methanol (10 ml) and hydrochloric acid (1.0 ml of a 4N solution in dioxane) added. After stirring at room temperature for 14 h, concentration under reduced pressure yielded the title compound (0.075 g).

Workup

  1. customremoved by filtration
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in methanol (10 ml)
  4. additionhydrochloric acid (1.0 ml of a 4N solution in dioxane) added
  5. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-4172df4453d7469ba75b57c73a30da87
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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