Hydrochloric Acid → 3,5-Dichlorobenzyl 4-(2-((2-hydroxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate
Reaction equation
C([O:3][C:4]1[C:7](=[O:8])[C:6](=[O:9])[C:5]=1[NH:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1)C.Cl>C1COCC1>[OH:9][C:6]1[C:7](=[O:8])[C:4](=[O:3])[C:5]=1[NH:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture comprising 3,5-dichlorobenzyl 4-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate (Example 3) (35 mg, 0.077 mmol) and 6M HCl (aq) (38.4 μl, 0.077 mmol) in THF (256 μl) was stirred overnight at room temperature. The reaction mixture was concentrated under pressure to give an aqueous suspension. The suspension was filtered, air dried and partitioned between EtOAc and water. The organic portion was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Further purification was carried out using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give an aqueous solution and then extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.