tert-butyl N-(2-benzylsulfanylethyl)carbamate

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

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

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

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

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

Procedure: N-Boc-2-Benzylsulfanyl-ethylamine (56 mg, 0.21 mmol) in 1 mL dry CH2Cl2 was treated with 0.5 mL of TFA at 0° C. After reaction completion (checked by TLC), the reaction mixture was concentrated in vacuo. The residue was dissolved in toluene and concentrated. This procedure was repeated two more times and the residue was dried under high vacuum and used directly in the next step without further purification. After reaction completion (checked by TLC) the reaction mixture was concentrated in vacuo The residue was dissolved in toluene concentrated the residue was dried under high vacuum used directly in the next step without further purification

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

Procedure: N-Boc-2-Tosyl-ethylamine (100 mg, 0.32 mmol) was added to a mixture of benzylmercaptan (45 mL, 0.38 mmol) and Cs2CO3 (68 mg, 0.21 mmol) in 1.6 mL of dry DMF. The reaction was stirred for 18 hours after which time the reaction mixture was poured onto water. The aqueous layer was extracted three times with AcOEt. The combined organic layers were washed with water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue was purified using SiO2 with AcOEt/Petroleum ether 5:95 to 15:75. A yellow oil was obtained (72 mg, 83%). NMR 1H (ppm, CDCl3): 7.31-7.25 (m, 5H), 4.79 (br. s., 1H), 3.70 (s, 2H), 3.25 (m, 2H), 2.55-2.53 (m, 2H), 1.43 (s, 9H). was poured onto water The aqueous layer was extracted three times with AcOEt The combined organic layers were washed with water, saturated NaHCO3 and brine dried over Na2SO4 concentrated The residue was purified A yellow oil was obtained (72 mg, 83%)

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

Procedure: N-Boc-2-Tosyl-ethylamine (100 mg, 0.32 mmol) was added to a mixture of benzylmercaptan (45 mL, 0.38 mmol) and Cs2CO3 (68 mg, 0.21 mmol) in 1.6 mL of dry DMF. The reaction was stirred for 18 hours after which time the reaction mixture was poured onto water. The aqueous layer was extracted three times with AcOEt. The combined organic layers were washed with water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated. The residue was purified using SiO2 with AcOEt/Petroleum ether 5:95 to 15:75. A yellow oil was obtained (72 mg, 83%). NMR 1H (ppm, CDCl3): 7.31-7.25 (m, 5H), 4.79 (br. s., 1H), 3.70 (s, 2H), 3.25 (m, 2H), 2.55-2.53 (m, 2H), 1.43 (s, 9H). was poured onto water The aqueous layer was extracted three times with AcOEt The combined organic layers were washed with water, saturated NaHCO3 and brine dried over Na2SO4 concentrated The residue was purified A yellow oil was obtained (72 mg, 83%)