Dichloromethane → 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2,5-dimethyl-1-(2-(1-methylethyl)-4-oxazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-isoxazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))-

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Reaction Steps

Using the procedure of Example 1U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl) amino)carbonyl)-L-valine with N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino) carbonyl)-L-alanine and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl) methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-5-amino-2-(N-((5-isoxazolyl)methoxy-carbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after silica gel chromatography using 92:8 CH2Cl2 :CH3OH, the desired compound (Rf 0.48, 92:8 CH2Cl2 :CH3OH) in 64% yield. 1H NMR (DMSO-d6) δ 1.08 (d, 3 H), 1.24 (d, 6 H), 1.50 (m, 2 H), 2.82 (s, 3 H), 3.0 (m, 1 H), 4.25 (s, 2 H), 4.60 (d, 1 H), 5.05 (s, 2 H), 6.20 (br d, 1 H), 6.32 (d, 1 H), 7.20 (m, 11 H), 7.50 (br d, 1 H), 7.78 (s, 1 H), 8.51 (d, 1 H). Mass spectrum: (M+H)+ =661.

Provenance & Evidence