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F
Bz
N
H
56f
2-Benzoylamino-3-(4-fluorophenyl)propionic acid prop-2-ynyl ester (56f). Prepared by
following general procedure A with: N-Bz-p-fluorophenylalanine (900 mg, 3.14 mmol),
propargyl alcohol (916 µL, 15.7 mmol), DCC (646 mg, 3.14 mmol), DMAP (36 mg, 0.30 mmol)
The reaction was performed in THF (15 mL) instead of CH2Cl2. Purification of the crude residue
after filtration by flash chromatography (gradient elution, hexanes-EtOAc, 20 : 1 to 3 : 1, v/v)
afforded 56f (503 mg, 42%).
1 H NMR (300 MHz, CDCl3): δ 7.73 (d, J = 7.7 Hz, 2H), 7.54-7.40 (m, 3H), 7.17-7.12 (m, 2H),
7.00-6.95 (m, 2H), 6.65 (d, J = 7.2 Hz, 1H), 5.14-5.08 (m, 1H), 4.83 (dd, J = 15.9, 2.2 Hz, 1H),
4.71 (dd, J = 15.3, 2.3 Hz, 1H), 3.31 (dd, J = 14.0, 5.7 Hz, 1H), 3.23 (dd, J = 14.0, 5.4 Hz, 1H),
2.56 (s, 1H); 13 C NMR (75 MHz, CDCl3): δ 170.7, 166.8, 163.7, 160.4, 133.6, 131.9, 131.2,
131.0, 130.9, 128.6, 126.9, 115.6, 115.3, 76.8, 75.7, 53.4, 52.9, 36.8; IR (thin film): ν 3298,
2933, 2129, 1749, 1644, 1510 cm -1 ; MS m/z (%) 325 (53), 269 (35), 204 (30), 160 (47), 105
(100); EI-HRMS calcd for C19H16NO3F m/z [M] + 325.1114; found 325.1110.
S
Bz
N
H
56g
2-Benzoylamino-3-thiophen-2-ylpropionic acid prop-2-ynyl ester (56g). Prepared by
following general procedure A with: N-Bz-(2-thienyl)-alanine (843 mg, 3.07 mmol), propargyl
alcohol (895 µL, 15.3 mmol), DCC (631 mg, 3.07 mmol), DMAP (36 mg, 0.30 mmol). The
reaction was performed in THF (20 mL) instead of CH2Cl2. Purification of the crude residue
after filtration by flash chromatography (gradient elution, hexanes-EtOAc, 20 : 1 to 1 : 1, v/v)
145
O
O
O
O