1,4-Dioxane hydrochloride → Ethyl carbamate guanidine
Reaction equation
[C:1]([NH:8][C:9]([NH:11]C(OC(C)(C)C)=O)=[NH:10])([O:3][C:4](C)(C)[CH3:5])=[O:2].Cl.O1CCOCC1>>[NH2:10][C:9]([NH2:11])=[NH:8].[C:1](=[O:2])([O:3][CH2:4][CH3:5])[NH2:8]Participants
3
Procedure
Ethylcarbazate (208 mg, 2 mmol) was added to a solution of N′N′-di-boc N″-triflylguanidine (800 mg, 2 mmol) in dichloromethane (10 mL). The mixture was stirred for overnight then diluted with EtOAc, washed with sodium bisulfat (2M), saturated sodium bicarbonate, dried over anhydrous NaSO4 and concentrated in vacuo. The crude residue was purified by flash column chromatography eluting with 30% EtOAc/hexane to afford a white solid (0.55 g). To this bis-boc guanidine was added 4M HCl/Dioxane (5 mL). The mixture was stirred for 24 hours and then concentrated to afford the title compound. 1H NMR (MeOD): δ 3.4.18 (d, 2H), 3.26 (s, 1H), 1.28 (t, 3H). MS (M+1) 134.
Workup
- concentration