Diethyl Ether → (S)-2-(phenoxathiine-2-sulfonylamino)-4-phenyl-butyric acid

Participants

Reaction Steps

The phenoxathiine-2-sulfonyl chloride (0.75 g, 2.52 mmol) was mixed with (L)-homo-phenylalanine (0.448 g, 2.52 mmol) and triethylamine (1.2 mL, 7.56 mmol) in 50 mL of water and 50 mL of tetrahydrofuran. The resulting mixture was stirred for 2 hours and then concentrated in vacuo. The residue was partitioned between 1 M HCl and ethyl acetate. The organic phase was dried over magnesium sulfate, and concentrated to give an oily solid. Trituration with diethyl ether gave (S)-2-(phenoxathiine-2-sulfonylamino)-4-phenyl-butyric acid as an off-white powder; mp 149-154° C.

Provenance & Evidence