Thiophenol → HCID 53954929, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of thiophenol (0.653 mL, 6.36 mmol) in THF (5 mL) was added sodium hydride (0.254 g, 6.36 mmol as a 60% mineral oil dispersion. The mixture was stirred for 10 minutes. A solution of Boc-homophenylalaninol benzenesulfonate (2.58 g, 6.36 mmol) in THF (5 mL) was added. The solution was stirred at room temperature for 10 minutes. Methanol (2 mL) was then added, and the mixture was heated at reflux for 1 hour. The solution was cooled, diluted with 1M NaOH (25 mL), extracted with CH2Cl2 (100 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (35 mL) and cooled to 0° C. To the solution was added 4-chloroperbenzoic acid (3.71 g, 13.99 mmol, estimated peracid content 65% by weight). The mixture was stirred for 1 hour, whereupon 10% NaOH (35 mL) and saturated aqueous NaHSO3 (35 mL) were added. The mixture was extracted with CH2Cl2 (3×50 mL portions), dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give a waxy solid, (S)-2-tert-butoxycarbonylamino-4-phenyl-1-phenylsulfonylbutane. TLC: (30% ethyl acetate/hexane) Rf =0.32. 1.25 g of this material was dissolved in CH2Cl2 (5 mL) and treated with HCl/dioxane (5 mL of a 4.0M solution). The mixture was stirred for 2 hours at room temperature. The solution was poured into ether (200 mL), forming an oily residue. The supernatant was discarded. The residue was again dissolved in CH2 Cl2 (10 mL), and poured into ether (200 mL). The intermediate, (S)-2-amino-4-phenyl-1-phenylsulfonylbutane hydrochloride precipitated out. The solid was filtered and dried in vacuo to give 0.40 g of material (38% yield from Boc-homophenylalaninol benzenesulfonate.

Provenance & Evidence