Methanol → Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, methyl ester, (alphaR,betaS)-

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Reaction Steps

The azide 10 (10 g, 24 mmol) was hydrogenated with 10% Pd/C (2.5 g) in methanol under H2 (50 p.s.i.) for 4 h. The solution was filtered, stood at 23° C. for 48 h, and concentrated. The solid was recrystallized over chloroform-methanol (50:1) to give 16 (5.5 g, 74%):[a]D20=-49 (c 1, CH3OH), lit. [a]D20=-49.6° (c 1, CH3OH); 1H NMR (CD3OD) d 3.68 (s, 3H), 4.60 (d, J=3.8 Hz, 1 H), 5.58 (d, J 3.8 Hz, 1 H), 7.32-7.61 (m, 8 H), 7.98-8.11 (m, 2 H).

Provenance & Evidence