{4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester → {4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]butyl}carbamic acid benzyl ester

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Reaction Steps

To a degassed solution of {4-[4-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester 320 (1.91 g, 4.1 mmol) and 1,2-dimethoxyethane (DME, 35 mL) was added 10% palladium on activated carbon (0.5 g, 50% wet). The mixture was hydrogenated overnight at 50 psi pressure. The catalyst was filtered through a pad of Celite and the solvent was evaporated in vacuo to provide 330 (1.78 g, 99%). 1H NMR (300 MHz, CDCl3) δ 1.42 (s, 9H), 1.58 (m, 4H), 2.59 (t, 4H), 3.17 (q, 2H), 3.47 (q, 2H), 5.18 (m, 3H), 5.58 (m, 1H), 5.70 (m, 1H), 7.07 (d, 2H), 7.33 (m, 5H), 7.49 (d, 2H).

Provenance & Evidence