2-Naphthylalanine → HCID 69654546, compound

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Reaction Steps

(A mixture of two diastereomers and their enantiomers.) To 2-(amino-phenyl-methyl)-5-bromo-hexanoic acid methyl ester in DMF was added Nal and NaHCO3 The resultant mixture was stirred in DMF at 100° C. for 1 hour, and then was cooled to room temperature and partitioned between ether and water. The organic layer was washed with brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography (97:3 CHCl3/MeOH) gave 1.63 g (90%) of the the product as an inseparable mixture of two diastereomers. 1H NMR (400 MHz, CDCl3) δ 7.17–7.32 (comp, 10H, both diastereomers), 4.47 (d, J=5.0 Hz, 1H), 3.97 (d, J=3.5 Hz, 1H), 3.45 (s, 3H), 3.38 (s, 3H), 3.02–3.08 (m, 1H), 2.92–2.99 (m, 1H), 2.75–2.85 (comp, 2H), 2.0–2.2 (comp, 2H), 1.80–2.00 (comp, 3H), 1.40–1.60 (comp, 2H), 1.20–1.30 (m, 1H), 1.20 (d, J=6.4 Hz, 3H), 1.07 (d, J=6.4 Hz, 3H); Mass spectrum m/e calcd. for M+H=234.1. Found 234.2.

Provenance & Evidence