Acetic Acid → HCID 131712095, compound

Participants

Reaction Steps

To a solution of Boc-Tyr-DAla-Phe-Met-OCH3 (5.8 g) (prepared in Step C of Example 1A) in 100 ml of dry tetrahydrofuran under nitrogen was added 1.0 g of LiBH4. After stirring at room temperature for 1 hour, 6 ml of acetic acid was added slowly followed by 50 ml of methanol to destroy excess LiBH4. Evaporation of the solution gave an oil which was dissolved in 250 ml of EtOAc and washed with 1 N HCl (4×25 ml), 1 N NaHCO3 (3×50 ml) and saturated NaCl (3×50 ml). Evaporation of the MgSO4 dried EtOAc solution gave a foam which was dissolved in 25 ml of hot EtOAc and diluted with 100 ml of hexane to give a solid. The solid was recrystallized from 50 ml of isopropanol and 100 ml of water to give 5.7 g (93%) of Boc-Tyr-DAla-Phe-Methioninol, m.p. 107-100° C., [α]D25 =0.08° (c, 1.00 in methanol).

Provenance & Evidence