Acetic Acid → HCID 18597298, compound

Participants

Reaction Steps

N[1-(R)-Carbomethoxy-3-methylthiopropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide (100 mg, 0.2 mM) was dissolved in MeOH (10 ml) and treated with IN NaOH (0.25 ml, 0.25 mM). After 18 h another portion of IN NaOH (0.5 ml, 0.5 mM) and H2O (2 ml) were added. After a further 18 h the reaction mixture was acidified with AcOH and evaporated in vacuo. The resulting white solid was chromatographed on C18 -Silica eluting with a gradient of 10% to 40% MeOH in H2O. The relevant fractions were pooled and evaporated in vacuo; the residue was recrystallised from hot H2O to yield the title compound (20 mg); m.p. 170-180; (Found: C,56.88; H,7.49; N,9.05; calculated for C22H35N3O5S,.0.6H2O: C,56.90; H,7.86; N,9.0 5%); νmax (Nujol) 3340, 1650 and 1625 cm-1 ; δ (d6DMSO) 0.82 (6H,t,J=7 Hz, (CH3)2CH), 1.17 and 1.5-1.9 (5H, m, CHCH(CH3)2 and SCH2CH2), 2.04 (3H, s,CH3S), 2.3 (2H, m, --SCH2), 2.6 (3H, d, J=5 Hz, NHCH3), 2.6-2.95 (3H, m, CH2C6H4 and α-CH),), 3.14 (1H, t, J=7 Hz, α-CH), 3.7 (3H, s, OCH3), 4.25 (1H, m, --CH), 6.8 and 7.12 (2×2H, each d, each J=9 Hz, C6H4), 7.88 (1H, q, J=5 Hz, NHCH3) and 8.18 (1H, d, J=9 Hz, NHCH); m/e 454 (100%, [m+1]+).

Provenance & Evidence