5-{2-Benzyloxy-4-[(E)-2-((S)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one → 5-{2-Hydroxy-4-[2-((R)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660666Notes

Reaction equation

HRID 660666 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][N:18]2[S:27]([CH3:30])(=[O:29])=[O:28])[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1)C1C=CC=CC=1>CCO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C@@H:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][N:18]2[S:27]([CH3:30])(=[O:28])=[O:29])[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1

Participants

4

Reactant 1

HCID 689963135-{2-Benzyloxy-4-[(E)-2-((S)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 577774225-{2-Hydroxy-4-[2-((R)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-ethyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 5-{2-benzyloxy-4-[(E)-2-((S)-2-methanesulfonyl-1,2,3,4-tetrahydroisoquinolin-3-yl)-vinyl]-phenyl}-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.090 g, 0.16 mmol) in EtOH (4 mL) is added a slurry of 10% Pd/C (0.1 g) in EtOH (6 mL). The reaction vessel is flushed twice with H2 and stirred at RT for 18 h under balloon pressure of H2. The mixture is filtered and purified by reverse phase chromatography using a gradient of 15 to 40% EtOH/water to afford the title compound as a white solid: LC retention time=1.0 min (Method A); (M+NH4)+=465.

Workup

  1. customThe reaction vessel is flushed twice with H2
  2. filtrationThe mixture is filtered
  3. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-307414afcf2f46b98007ff3d64ba7a53
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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