(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

HRID 2411411Notes

Reaction equation

HRID 2411411 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=3[CH3:39])[CH2:28][CH2:27]2)=[O:25])=[C:20]([S:40]([CH3:43])(=[O:42])=[O:41])[CH:19]=1>>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:27][CH2:28][N:29]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=3[CH3:39])[CH2:30][CH2:31]2)=[O:25])=[C:20]([S:40]([CH3:43])(=[O:41])=[O:42])[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxideHCID 58484856(4-Bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 71252629(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneYield 70.1%

Procedure

Using (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (536 mg) described in Preparation Example 1 and (4-bromo-2-methanesulfonylphenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1.0 g) described in Preparation Example 110 and by the reaction and treatment in the same manner as in Example 4, the title compound (950 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 110 and by the reaction and treatment in the same manner as in Example 4

Sources & evidence

ORD record
ord-be0226224973498498085d22db5ab34e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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