(2S,5R)-tert-butyl 5-(benzyloxy(chlorocarbonyl)amino)-2-(1,2,4-thiadiazol-5-yl)piperidine-1-carboxylate → ((3R,6S)-6-(1,2,4-thiadiazol-5-yl)piperidin-3-yl)(benzyloxy)carbamic chloride HCl salt
Reaction equation
[CH2:1]([O:8][N:9]([C:28]([Cl:30])=[O:29])[C@H:10]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]2[S:27][N:26]=[CH:25][N:24]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[ClH:30].[S:27]1[C:23]([C@H:13]2[NH:14][CH2:15][C@H:10]([N:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:28]([Cl:30])=[O:29])[CH2:11][CH2:12]2)=[N:24][CH:25]=[N:26]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(2S,5R)-tert-butyl 5-(benzyloxy(chlorocarbonyl)amino)-2-(1,2,4-thiadiazol-5-yl)piperidine-1-carboxylate was dissolved in 4 N HCl in dioxane (10 mL). The mixture was stirred at rt for 0.5 h and then concentrated to provide the crude ((3R,6S)-6-(1,2,4-thiadiazol-5-yl)piperidin-3-yl)(benzyloxy)carbamic chloride HCl salt, which was directly used in the next step. ESI-MS (EI+, m/z): 445 [M+H]+.