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ChemicalBook CAS DataBase List S-BENZYL-N-BOC-ETHANETHIOLAMINE

S-BENZYL-N-BOC-ETHANETHIOLAMINE synthesis

4synthesis methods
-

Yield:873330-01-9 83%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide; for 18 h;

Steps:

67.C

67C: N-Boc-2-Benzylsulfanyl-ethylamine; N-Boc-2-Tosyl-ethylamine (100 mg, 0.32 mmol) was added to a mixture of benzylmercaptan (45 mL, 0.38 mmol) and CsaCOs (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 NaHCOs and brine, dried over Na2SC>4 and concentrated. The residue was purified using SiC>2 with AcOEt/Petroleum ether 5:95 to 15:75. A yellow oil was obtained (72 mg, 83%). NMR 'H (ppm, CDC13): 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).

References:

WO2006/2474,2006,A1 Location in patent:Page/Page column 174