Hydrochloric Acid → N-{2-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-benzamide

HRID 660534Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][NH:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[N:17](CC[Si](C)(C)C)[S:16]1(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:29][CH2:30][NH:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:19][C:18](=[O:20])[NH:17][S:16]1(=[O:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}ethyl)-benzamide (0.13 g, 0.23 mmol) in 3 mL THF is added 0.7 mL of a 0.5M solution of TBAF in THF. The mixture is stirred at 50° C. for 2 h then is allowed to cool to RT. The mixture is poured into 1N HCl (20 mL) and extracted with EtOAc. The organic phase is washed with 1N HCl and brine and is dried over magnesium sulfate. The solvent is removed under reduced pressure and the resulting solid is triturated with ether/hexane to furnish the title compound.

Workup

temperatureto cool to RT
extractionextracted with EtOAc
washThe organic phase is washed with 1N HCl and brine
dry with materialis dried over magnesium sulfate
customThe solvent is removed under reduced pressure
customthe resulting solid is triturated with ether/hexane

Sources & evidence

ORD record: ord-cf4d267e2c4e43c9a4d4ae3694cb0bb0
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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