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1H), 1.84 (dd, J = 7.1, 3.2 Hz, 3H), 0.36 (s, 9H); 13 C NMR (75 MHz, CDCl3): δ 203.3, 171.6,
151.6, 135.5, 130.0, 128.1, 126.9, 97.6, 92.3, 91.6, 90.9, 64.1, 52.9, 39.7, 13.7, -0.8; IR (thin
film): ν 3397, 2955, 2165, 1968, 1741, 1662 cm -1 ; EI-HRMS calcd for C20H25NO3Si m/z [M] +
355.1604; found 355.1589.
O
HN
MeO 2C Bn
Methyl 2-(3-phenylpropiolamido)-2-benzylhexa-3,4-dienoate (145d). To a solution of amine
152 (131 mg, 567 µmol) in CH2Cl2 (4 mL) was added 3-phenylpropiolic acid (83 mg, 568 µmol)
and DCC (117 mg, 570 µmol). The reaction mixture was stirred for 30 min, and then filtered to
remove the white solid. The solution was concentrated under vacuum and the resulting oil
•
145d
purified by flash chromatography to afford 145d (112 mg, 55%).
1 H NMR (300 MHz, CDCl3): δ 7.63-7.61 (m, 2H), 7.53-7.30 (m, 6H), 7.25-7.23 (m, 2H), 6.66 (s,
1H), 5.60–5.55 (m, 1H), 5.52-5.44 (m, 1H), 3.90 (s, 3H), 3.78 (d, J = 13.7 Hz, 1H), 3.53 (d, J =
13.7 Hz, 1H), 1.81 (dd, J = 7.1, 3.1 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ 203.3, 171.7, 152.3,
135.6, 132.6, 130.1, 130.0, 128.4, 128.2, 127.0, 120.1, 92.4, 91.7, 84.2, 83.1, 64.1, 53.0, 39.8,
13.8; IR (thin film): ν 3393, 3292, 2950, 2214, 1968, 1741, 1654 cm -1 ; EI-HRMS calcd for
C23H21NO3 m/z [M] + 359.1521; found 359.1526.
Bz
O
N
MeO 2C Bn
145e
2-[Benzoyl-(1-oxobut-2-ynyl)-amino]-2-benzylhexa-3,4-dienoic acid methyl ester (145e). To
a solution of 145a (0.15 g, 0.49 mmol), in 1,2-dichloroethane (5 mL) were added Et3N (0.399
mL, 2.44 mmol), DMAP (catalytic amount ~ 10 mg), and 4Å molecular sieves (0.5 g) at rt.
204
•
Ph
H
H