tert-butyl N-[2-(carbamothioylamino)ethyl]carbamate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of (2-thioureido-ethyl)-carbamic acid tert-butyl ester [CAS 331779-96-5] (3.6 g), 3-bromo-2-butanone (2.45 g), and DIPEA (5.5 ml) in ethanol (100 ml) was stirred overnight at RT and refluxed 1 hour. The mixture was concentrated. Ethyl acetate was added. Insoluble parts were filtered off and the remaining solution was extracted with brine. The organic layer was dried, evaporated and purified by flash chromatography yielding after crystallization 0.86 g of white crystals. MS (ISP): 272.2 (MH+). refluxed 1 hour The mixture was concentrated Ethyl acetate was added Insoluble parts were filtered off the remaining solution was extracted with brine The organic layer was dried evaporated purified by flash chromatography yielding after crystallization 0.86 g of white crystals

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of (2-thioureido-ethyl)-carbamic acid tert-butyl ester [CAS 331779-96-5] (3.6 g), 3-bromo-2-butanone (2.45 g), and DIPEA (5.5 ml) in ethanol (100 ml) was stirred overnight at RT and refluxed 1 hour. The mixture was concentrated. Ethyl acetate was added. Insoluble parts were filtered off and the remaining solution was extracted with brine. The organic layer was dried, evaporated and purified by flash chromatography yielding after crystallization 0.86 g of white crystals. MS (ISP): 272.2 (MH+). refluxed 1 hour The mixture was concentrated Ethyl acetate was added Insoluble parts were filtered off the remaining solution was extracted with brine The organic layer was dried evaporated purified by flash chromatography yielding after crystallization 0.86 g of white crystals

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of (2-thioureido-ethyl)-carbamic acid tert-butyl ester [CAS 331779-96-5] (3.6 g), 3-bromo-2-butanone (2.45 g), and DIPEA (5.5 ml) in ethanol (100 ml) was stirred overnight at RT and refluxed 1 hour. The mixture was concentrated. Ethyl acetate was added. Insoluble parts were filtered off and the remaining solution was extracted with brine. The organic layer was dried, evaporated and purified by flash chromatography yielding after crystallization 0.86 g of white crystals. MS (ISP): 272.2 (MH+). refluxed 1 hour The mixture was concentrated Ethyl acetate was added Insoluble parts were filtered off the remaining solution was extracted with brine The organic layer was dried evaporated purified by flash chromatography yielding after crystallization 0.86 g of white crystals

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was synthesised from (2-Thioureido-ethyl)-carbamic acid tert-butyl ester and Dimethylformamide dimethyl acetal according to the procedure described for Example C in 51% yield. MS (m/e): 275.4 (MH+, 100%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-(2-t-butyloxycarbonylaminoethyl)thiourea (1.00 g, 4.54 mol) in ethanol (22 mL) was added 1,3-dichloroacetone (2.60 g, 20.47 mmol) at room temperature. After 2 hours the reaction mixture was concentrated under reduced pressure. The residue was triturated with ether and filtered to afford the solid precipitate of title product (1.40 g), which was used for next step without further purification. 1H NMR (CDCl3) δ 1.40 (s, 9H), 3.35 (m, 4H), 4.38 (s, 2H), 5.00 (br s, 1H), 6.40 (s, 1H). After 2 hours the reaction mixture was concentrated under reduced pressure The residue was triturated with ether filtered

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-benzoyl-N′-(2-t-butyloxycarbonylaminoethyl)thiourea (1.50 g, 0.44 mmol) was suspended in aqueous sodium hydroxide solution (22 mL, 2.0 M) and heated to 50° C. with stirring for 1 hour, which resulted in dissolution of starting material and consequent formation of precipitate. Reaction mixture was extracted with ethyl. acetate and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford solid residue of title product (1.01 g), which was used for next step without further purification. 1H NMR (CDCl3/CD3OD) δ 1.40 (s, 9H), 3.20 (m, 4H), 3.55 (m, 2H). which resulted in dissolution of starting material and consequent formation of precipitate Reaction mixture was extracted with ethyl acetate and the organic layer was dried over sodium sulfate concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of (2-thioureido-ethyl)-carbamic acid tert-butyl ester [CAS 331779-96-5] (3.6 g), 3-bromo-2-butanone (2.45 g), and DIPEA (5.5 ml) in ethanol (100 ml) was stirred overnight at RT and refluxed 1 hour. The mixture was concentrated. Ethyl acetate was added. Insoluble parts were filtered off and the remaining solution was extracted with brine. The organic layer was dried, evaporated and purified by flash chromatography yielding after crystallization 0.86 g of white crystals. refluxed 1 hour The mixture was concentrated Ethyl acetate was added Insoluble parts were filtered off the remaining solution was extracted with brine The organic layer was dried evaporated purified by flash chromatography yielding after crystallization 0.86 g of white crystals