1,4-Dioxane hydrochloride → Ethyl carbamate guanidine

HRID 852309Notes

Reaction equation

HRID 852309 reaction equation
[C:1]([NH:8][C:9](=[NH:18])[NH:10]C(OC(C)(C)C)=O)([O:3][C:4](C)(C)[CH3:5])=[O:2].Cl.O1CCOCC1>>[NH2:10][C:9]([NH2:18])=[NH:8].[C:1](=[O:2])([O:3][CH2:4][CH3:5])[NH2:8]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

Product 1

HCID 22713682Ethyl carbamate guanidine

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

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd86c59035a46568bc45aea9a3483da
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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