Hydrochloric Acid → 5-[2-Benzyloxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660798Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[N:25]1[S:29](=[O:31])(=[O:30])[N:28](CC[Si](C)(C)C)[C:27](=[O:38])[CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].Cl>CN(C=O)C.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[N:25]1[S:29](=[O:31])(=[O:30])[NH:28][C:27](=[O:38])[CH2:26]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-[2-benzyloxy-4-(2-methoxymethylbenzyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (375 mg, 0.679 mmol) in DMF (5 mL) is added CsF (361 mg, 2.37 mmol) and the mixture is stirred at 65° C. for 3 h. The mixture is diluted with EtOAc and water then is acidified with 1N HCl. The organic phase is washed with 1N HCl, water and brine. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure to give the title compound as a foam.

Workup

washThe organic phase is washed with 1N HCl, water and brine
dry with materialThe organic phase is dried over sodium sulfate
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-96e1e06e275d47c7ac8136df3d3af949
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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