(S)-3-benzyloxymethylisothiazolidine 1,1-dioxide → methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoate

HRID 2411135Notes

Reaction equation

HRID 2411135 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1.[CH2:19]([O:26][CH2:27][C@@H:28]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[NH:29]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([O:26][CH2:27][C@@H:28]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[N:29]1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 16664117(S)-3-benzyloxymethylisothiazolidine 1,1-dioxideHCID 58484624Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

Product 1

HCID 71261161methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoateYield 87.1%

Procedure

Using methyl 4-bromo-2-(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate (334 mg) described in Preparation Example 13 and (S)-3-benzyloxymethylisothiazolidine 1,1-dioxide (241 mg) described in Preparation Example 1 and by the reaction and treatment in the same manner as in Preparation Example 12, the title compound (430 mg) was obtained.

Workup

  1. customdescribed in Preparation Example 1 and by the reaction and treatment in the same manner as in Preparation Example 12

Sources & evidence

ORD record
ord-b28c3456080d49809963bea175e9f485
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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