L-Phenylalanine → 2768-53-8

Temperature

0 °C

To a solution of L-phenylalanine (0.33 g, 2.0 mmol) in 0.20M potassium carbonate (20 mL) and acetonitrile (30 mL) was added dropwise a solution of N-benzyloxycarbonyl-L-alanine N-carboxyanhydride (0.45 g, 1.8 mmol) in acetonitrile (5 mL) at 0° C. The mixture was stirred 40 min at 0° C. and diluted with ethyl acetate (50 mL) and 1M hydrochloric acid (10 mL). The layers were separated and the aqueous layer extracted with ethyl acetate (2×35 mL). The combined organic fractions were washed with brine (30 mL), 0.5M hydrochloric acid (2×50 mL) and water (2×50 mL), dried (MgSO4) and concentrated. The residue was recrystallized from chloroform/hexane to give 0.26 g (39%) of N-benzyloxycarbonyl-L-alanyl-L-phenylalanine: mp 121°-122° C.; NMR (DMSO-d6) δ 12.71 (s, 1H), 8.06 (m, 1H), 7.30 (m, 5H), 5.01 (s, 2H), 4.43 (m, 1H), 4.06 (m, 1H), 2.99 (m, 2H), 11.19 (d, 2H, J=7 Hz).

1. customThe layers were separated
2. extractionthe aqueous layer extracted with ethyl acetate (2×35 mL)
3. washThe combined organic fractions were washed with brine (30 mL), 0.5M hydrochloric acid (2×50 mL) and water (2×50 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe residue was recrystallized from chloroform/hexane

ORD record

ord-e20bfb5c46c8464bace2dffc1cb221f3

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04946942