Acetic Acid → HCID 131711966, compound

Participants

Reaction Steps

D-Threonine (4.58 g, 38.5 mmol) was dissolved in 19 ml of 40% Triton B and evaporated to an oil. It was re-evaporated twice from DMF, and the salt obtained was stirred with Boc-Tyr-OSu (13.24 g, 35 mmol) in DMF (80 ml) at 0° C. for 1.5 hr and at 25° C. for 30 hr. A constant pH of 8 was maintained by dropwise addition of Et3N during reaction time. The reaction was acidified to pH 4 with acetic acid. The solvent was evaporated to a syrup, dissolved in chloroform, washed with 0.5 N H2SO4 and water, dried (Na2SO4) and evaporated to low volume. The product was obtained as an amorphous solid from petroleum ether: 9.17 g (68.5%): [α]D25 -42.9° (c 1.4, DMF).

Provenance & Evidence