(2S,9R)-7-Benzyl-2-[(tert-butoxycarbonyl)amino]-10-cyano-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester → (2S, 9R)-2-[(tert-Butoxycarbonyl)amino]-11-amino-9-hydroxy-7-azaundecanoic Acid tert-Butyl Ester, Diacetate Salt

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Reaction Steps

The Nεbenzyl nitrile (26) (4.80 g, 10.7 mmol) was dissolved in glacial acetic acid (100 ml); 10% Pd—C (0.50 g) and PtO2 (1.00 g) were added; and hydrogen gas was introduced. The reaction was complete after 6 hours, and the catalyst was filtered through a bed of Celite and washed with acetic acid. The filtrate was concentrated in vacuo. Azeotropic removal of the acetic acid with toluene gave (27) as a colorless oil (5.10 g, 99%) 1H NMR (500 MHz) (CD3OD) d 4.02-3.94 (m, 2H), 3.14-2.86 (m, 6H), 1.94 (s, 6H), 1.87-1.58 (m, 8H), 1.46 (s, 9H), 1.44 (s, 9H). 13C NMR (CD3OD) δ169.6, 156.54, 85.3, 70.2, 62.6, 56.6, 54.2, 53.9, 34.0, 31.1, 28.2, 26.3, 23.2. HRMS m/z calcd. for C19H40N3O5 390.2968, found 390.2977. [α]25D+0.6° (c=1.00, CH3OH).

Provenance & Evidence