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

HRID 660667Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C@@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][NH:18]2)[CH:12]=[CH:11][C:10]=1[N:27]1[S:31](=[O:33])(=[O:32])[N:30](CC[Si](C)(C)C)[C:29](=[O:40])[CH2:28]1)C1C=CC=CC=1.[C:41]1([S:47](Cl)(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[C:41]1([S:47]([N:18]2[C@H:17]([CH2:16][CH2:15][C:13]3[CH:12]=[CH:11][C:10]([N:27]4[S:31](=[O:33])(=[O:32])[NH:30][C:29](=[O:40])[CH2:28]4)=[C:9]([OH:8])[CH:14]=3)[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 688396835-{2-Benzyloxy-4-[(E)-(S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577774665-{4-[2-((R)-2-Benzenesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-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)-(S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and benzenesulfonyl chloride analogous to Example 200, steps F, G and H: LC retention time=1.26 min (Method A); (M+NH4)+=545.

Sources & evidence

ORD record: ord-4981bd6809324b98ac43ea86c6254252
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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