Acetic Acid → Boc-Thr(Bzl)-Pro-OH

Participants

Reaction Steps

A suspension of H-Pro-OH (1.0 g, 8.69 mmol) in DMF (15 ml) was stirred with Et3N (2.44 ml) and Boc-Thr(Bzl)-OSu (3.88 g, 9.56 mmol) at 0° C for 1 hr and 25° C for 72 hrs. The reaction was acidified to pH 3 with acetic acid and worked up as described in Example 2 to produce a crystalline product from EtOAc and petroleum ether: 3.0 g (85.0%); mp 84°-88° C; [α]D25 -52.2° (c 1, CHCl3). Anal. Calcd for C21H30N2O6 (406.48): C, 62.05; H, 7.43; N, 6.89. Found: C, 62.29; H, 7.52; N, 6.86.

Provenance & Evidence