Benzenesulfonyl chloride → 5-{4-[2-(1-Benzenesulfonylpiperidin-2-yl)-ethyl]-2-hydroxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660652Notes

Reaction equation

HRID 660652 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[CH:11][C:10]=1[N:23]1[S:27](=[O:29])(=[O:28])[N:26](CC[Si](C)(C)C)[C:25](=[O:36])[CH2:24]1)C1C=CC=CC=1.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:37]1([S:43]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]2[CH2:16][CH2:15][C:13]2[CH:12]=[CH:11][C:10]([N:23]3[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:36])[CH2:24]3)=[C:9]([OH:8])[CH:14]=2)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 68842724HCID 68842724, compound

Product 1

HCID 577773335-{4-[2-(1-Benzenesulfonylpiperidin-2-yl)-ethyl]-2-hydroxyphenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Procedure

The title compound is prepared from 5-[2-benzyloxy-4-(E)-2-piperidin-2-yl-vinyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 92, step A) and benzenesulfonyl chloride analogous to Example 193: LC retention time=1.28 min (Method A); (M−1)−=478.

Sources & evidence

ORD record
ord-4d9d956409f044a68a511ad6f43127f4
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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