1-isocyanatododecane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.1 mole of 2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline is dissolved in 50 ml of ether and the solution is mixed with 0.1 mole of n-dodecyl isocyanate. A spatula tip of diazadicyclooctane is then added, the mixture is left to stand for 7 days at 20° to 25° C. and cooled at -70° C. and the precipitate which has separated out is filtered off. N-n-Dodecylaminocarbonyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline with a melting point of 48°-50° C. is obtained. Yield: 66% of theory. A spatula tip of diazadicyclooctane is then added the mixture is left the precipitate which has separated out is filtered off

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g of the compound from Example 1 are suspended in 160 ml of tetrahydrofuran and 40 ml of ethanol. 4.3 g of dodecyl isocyanate, dissolved in 20 ml of tetrahydrofuran, are added dropwise to this suspension in the course of 20 minutes. When the reaction has ended, the mixture is evaporated in vacuo and the resulting syrup is purified by column chromatography (mobile phase methylene chloride/methanol, 15:1) are added dropwise to this suspension in the course of 20 minutes the mixture is evaporated in vacuo the resulting syrup is purified by column chromatography (mobile phase methylene chloride/methanol, 15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g of the compound from Example 1 are suspended in 160 ml of tetrahydrofuran and 40 ml of ethanol. 4.3 g of dodecyl isocyanate, dissolved in 20 ml of tetrahydrofuran, are added dropwise to this suspension in the course of 20 minutes. When the reaction has ended, the mixture is evaporated in vacuo and the resulting syrup is purified by column chromatography (mobile phase methylene chloride/methanol, 15:1) are added dropwise to this suspension in the course of 20 minutes the mixture is evaporated in vacuo the resulting syrup is purified by column chromatography (mobile phase methylene chloride/methanol, 15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glycine (0.40 g, 5.25 mmol) and 0.91 mL of diisopropylethylamine (5.25 mmol) were dissolved in 4 mL DMF and 6 mL water. Dodecylisocyanate (0.72 mL, 3.0 mmol) in 7 mL tetrahydrofuran was added and the mixture was stirred for 1 h at room temperature. Water (40 mL) was added and the resulting mixture was washed with ethyl acetate twice. The aqueous layer was acidified with 6N HCl, the resulting precipitate was filtered, and then dried to provide 575 mg of the title compound. the resulting mixture was washed with ethyl acetate twice the resulting precipitate was filtered dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glycine (0.40 g, 5.25 mmol) and 0.91 mL of diisopropylethylamine (5.25 mmol) were dissolved in 4 mL DMF and 6 mL water. Dodecylisocyanate (0.72 mL, 3.0 mmol) in 7 mL tetrahydrofuran was added and the mixture was stirred for 1 h at room temperature. Water (40 mL) was added and the resulting mixture was washed with ethyl acetate twice. The aqueous layer was acidified with 6N HCl, the resulting precipitate was filtered, and then dried to provide 575 mg of the title compound. the resulting mixture was washed with ethyl acetate twice the resulting precipitate was filtered dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dodecylisocyanate (105 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (Compound 2, 70 mg, 0.33 mmol) and triethylamine (69 microliter, 0.49 mmol) in tetrahydrofuran (3 ml) at room temperature. After stirring at room temperature overnight (ca. 16 hours), the reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane. Fractions of Rf of about 0.47 on evaporation gave the title urea as an off-white solid. the reaction mixture was quenched with water Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane Fractions of Rf of about 0.47 on evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dodecylisocyanate (105 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (Compound 2, 70 mg, 0.33 mmol) and triethylamine (69 microliter, 0.49 mmol) in tetrahydrofuran (3 ml) at room temperature. After stirring at room temperature overnight (ca. 16 hours), the reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane. Fractions of Rf of about 0.47 on evaporation gave the title urea as an off-white solid. the reaction mixture was quenched with water Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane Fractions of Rf of about 0.47 on evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dodecylisocyanate (105 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (Compound 2, 70 mg, 0.33 mmol) and triethylamine (69 microliter, 0.49 mmol) in tetrahydrofuran (3 ml) at room temperature. After stirring at room temperature overnight (ca. 16 hours), the reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane. Fractions of Rf of about 0.47 on evaporation gave the title urea as an off-white solid. the reaction mixture was quenched with water Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave a residue which was purified by flash chromatography on silica using 60% ethyl ether/hexane Fractions of Rf of about 0.47 on evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 ml dodecyl isocyanate and 2.4 ml of ethylene glycol are combined in tetrahydrofuran at room temperature and stirred overnight at room temperature. The resultant material is evaporated under reduced pressure (<30° C.), dried in vacuo, and purified by chromatography on a silica gel column using ethyl acetate as elutant. Fractions 74-94 are combined (Rf 0.75 TLC Silica gel ethyl acetate iodine detection), evaporated under reduced pressure (<30° C.) and dried in vacuo to yield 546 mg of title product. The resultant material is evaporated under reduced pressure (<30° C.) dried in vacuo purified by chromatography on a silica gel column evaporated under reduced pressure (<30° C.) dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 ml dodecyl isocyanate and 2.4 ml of ethylene glycol are combined in tetrahydrofuran at room temperature and stirred overnight at room temperature. The resultant material is evaporated under reduced pressure (<30° C.), dried in vacuo, and purified by chromatography on a silica gel column using ethyl acetate as elutant. Fractions 74-94 are combined (Rf 0.75 TLC Silica gel ethyl acetate iodine detection), evaporated under reduced pressure (<30° C.) and dried in vacuo to yield 546 mg of title product. The resultant material is evaporated under reduced pressure (<30° C.) dried in vacuo purified by chromatography on a silica gel column evaporated under reduced pressure (<30° C.) dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the synthetic procedure of 6a as described in Example 1, compound 6g (78% yield) was synthesized from benzo[d]isothiazol-3-one and dodecyl isocyanate as a white solid. mp 66-67° C.; IR(CHCl3) 3279, 1709, 1660, 1536 cm−1; 1H-NMR (CDCl3) δ0.87 (t, J=6.8 Hz, 3H), 1.20-1.39 (m, 18H), 1.59-1.66 (m, 2H), 3.40-3.46 (m, 2H), 7.42 (t, J=7.6 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.69 (t, J=7.6 Hz, 1H), 8.01 (d, J=7.6 Hz, 1H), 8.87 (br s, 1H); ESIMS m/e 363 (M++1).