Hydrochloric Acid → HCID 131711187, compound

Participants

Reaction Conditions

Reaction Steps

Compound II (3.13 g, 4.33 mmol) was dissolved in DMF (50 ml, purged with Argon for 15 min), cooled to -20° C and treated with 5.93 ml of 4 N HCl in THF followed by 0.88 ml of i-amylnitrite. After 30 min, the mixture was cooled down to -30° C and 3.64 ml of Et3N and H-Thr(Bzl)-Ser(Bzl)-Glu(OBzl)-Lys(Z)-OH were added. The mixture was stirred at 4° C for 72 hours during which time some more Et3N was added in order to maintain the pH between 7 and 8. The reaction was acidified to pH 3 with acetic acid. Evaporation of the solvent and trituration of the residue in water gave a white glassy product which was washed with 5% AcOH and water; it was then triturated in EtOH several times and dried, yield 5.5 g (81.5%); mp 227°-231° C dec. [α]D25 - 3.2° (c 1, DMF). Anal. Calcd for C82H96N10O19S (1157.79): C, 63.22; H, 6.21; N, 8.99; S, 2.06. Found: C, 63.03; H, 6.24; N, 9.12; S, 2.12. Amino acid Analysis (6N HCl/phenol, 100° C, 24 hr): Lys, 1.11; Thr, 1.05; Ser, 0.86; Glu, 1.07; Gly, 1.86; Met, 0.95; Tyr, 0.81; Phe, 1.02.

Provenance & Evidence