Hydrochloric Acid → Boc-Asn-Ala-OBzl

Participants

Reaction Steps

The HCl salt of H-Ala-OBzl (43 g, 200 mmol) was dissolved in DMF (500 ml) and stirred with Boc-Asn-OH (46.5 g, 200 mmol), NMM (27 ml), HOBt (54 g), and DCC (45 g) at 0° C for 1.5 hr and 25° C for 17 hr. The reaction mixture was worked up as in Example 11 to a solid which was crystallized from tetrahydrofuran and minimum petroleum ether: 62.5 g (79.4%); mp 140°-141° C; [α]D25 -31.1° (c 1, MeOH). Anal. Calcd for C19H27N3O6 (393.44): C, 58.00; H, 6.92; N, 10.68. Found: C, 57.77; H, 7.09; N, 10.52.

Provenance & Evidence