(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1,3-thiazol-2-yl)propanoic acid → Boc-beta-(2-Thiazolyl)alanyl-Ndelta-Boc-Nalpha-Methylornithine beta-Naphthylamide

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Reaction Steps

Boc-β-(2-thiazolyl)alanine and Nδ-Boc-Nα-methylornithine β-naphthylamide were coupled under the conditions described in Procedure B, afforded a glassy solid which was purified by silica gel chromatography (1 to 2% MeOH/CH2Cl2): 1H NMR (400 MHz, CDCl3) δ1.45 (s, 9H), 1.50 (s, 9H), 1.52 (m, 2H), 1.77 (m, 1H), 2.18 (m, 1H), 3.01 (s, 3H), 3.19 (m, 3H), 3.49 (m, 1H), 4.98 (m,1H), 5.36 (m, 1H), 7.12 (s, 1H), 7.43 (m, 2H), 7.59 (d, J=7.2 Hz, 1H), 7.78 (m, 3H), 8.28 (s, 1H), 8.58 (s, 1H); mass spectrum (ES+) m/e 626 (M+1).

Provenance & Evidence