Cesium fluoride → 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

HRID 660665Notes

Reaction equation

[CH2:1]([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])[N:34](CC[Si](C)(C)C)[C:33](=[O:44])[CH2:32]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([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:36])(=[O:37])[NH:34][C:33](=[O:44])[CH2:32]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

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-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (0.107 g, 0.164 mmol) in DMF (10 mL) is added CsF (0.980 g, 6.47 mmol). The mixture is stirred at 60° C. for 1.25 h, and then diluted with EtOAc (20 mL) and washed with 1N HCl (2×15 mL), followed by brine (2×15 mL). The organic layer is dried with Na2SO4 and the solvent removed under reduced pressure to give the title compound.

Workup

washwashed with 1N HCl (2×15 mL)
dry with materialThe organic layer is dried with Na2SO4
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-3b4e5b92bc084b319035f266deaa4915
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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