Thiazole → Thiazol-5-ylmethyl ((1S,2S,4S)-1-benzyl-4-(((1,1-dimethylethoxy)carbonyl)amino)-2-hydroxy-5-phenylpentyl)carbamate

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Reaction Steps

The product of Example 68D (6.0 g, 15.6 mmoles) was dissolved in 60 ml of DMF under nitrogen atmosphere. To this stirred solution at room temperature was added 5-p-nitrophenyloxycarbonyloxymethyl)thiazole (4.67 g, 15.6 mmole) and the resulting solution was stirred for 4 h. The solvent was removed under reduced pressure by rotary evaporation and the residue dissolved in 150 mL EtOAc. This solution was washed with 5×75 mL 1N NaOH solution, 100 mL brine, dried over Na2SO4. The solvent was removed to afford 8.02 g of a slightly yellowish oil. This material was crystallized from 30 mL EtOAc and 40 mL hexane to afford 6.53 g (80%) of the desired product as a white solid. mp 118°-120° C. H 1NMR (CDCl3) δ8.79 (s, 1H), 7.83 (s, 1H), 7.30-7.15 (m, 8H), 7.08 (m, 2H), 5.23 (s, 2H), 5.14 (d, 1H, J=9 Hz), 4.52 (m, 1H), 3.92-3.72 (m, 3H), 3.65 (m, 1H), 2.85 (d-apparent 2H, J=7.5 Hz), 2.72 (d-apparent, 2H, J=7 Hz), 1,61 (m, 2H), 1.38 (s, 9H). CIMS m/z (526) (M+H)+, 543 (M+18)+.

Provenance & Evidence