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afforded 56g (500 mg, 52%).
1 H NMR (300 MHz, CDCl3): δ 7.80-7.78 (m, 2H), 7.54-7.41 (m, 3H), 7.19-7.17 (m, 1H), 6.96-
6.83 (m, 3H), 5.13 (dt, J = 7.5, 5.0 Hz, 1H), 4.81 (dd, J = 15.9, 2.3 Hz, 1H), 4.74 (dd, J = 15.5,
2.3 Hz, 1H), 3.54 (d, J = 4.9 Hz, 2H), 2.55547 (t, J = 2.3 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ
170.3, 166.8, 136.8, 133.6, 131.8, 128.5, 127.0, 125.0, 76.7, 75.8, 53.2, 53.0, 31.8; IR (thin film):
ν 3291, 2932, 2853, 2129, 1748, 1645, 1531 cm -1 ; MS m/z (%) 313 (7), 230 (5), 192 (53), 105
(100); EI-HRMS calcd for C17H15NO3S m/z [M] + 313.0773; found 313.0774.
Boc
N
Bz
N
H
56h
3-(2-Benzoylamino-2-prop-2-ynyloxycarbonylethyl)indole-1-carboxylic acid tert-butyl ester
(56h). Prepared by following general procedure A with: N-Bz-(3-N-Boc-indolyl)-alanine (600
mg, 1.47 mmol), propargyl alcohol (429 µL, 7.35 mmol), DCC (303 mg, 1.47 mmol), DMAP (10
mg, 0.08 mmol). Purification of the crude residue after filtration by flash chromatography
(gradient elution, hexanes-EtOAc, 1 : 0 to 2 : 1, v/v) afforded 56h (430 mg, 66%).
1 H NMR (300 MHz, CDCl3): δ 8.12 (d, J = 7.9 Hz, 1H), 7.71-7.69 (m, 2H), 7.54-7.16 (m, 7H),
6.73 (d, J = 7.4 Hz, 1H), 5.21 (dt, J = 7.4, 5.2 Hz, 1H), 4.78 (dd, J = 15.5, 2.4 Hz, 1H), 4.69 (dd,
J = 15.5, 2.4 Hz, 1H), 3.50-3.37 (m, 2H), 2.56 (t, J = 2.3 Hz, 1H), 1.65 (s, 9H); 13 C NMR (75
MHz, CDCl3): δ 170.9, 167.0, 149.5, 135.3, 133.7, 131.8, 130.5, 128.5, 127.1, 124.6, 124.5,
122.6, 118.9, 115.3, 114.6, 83.7, 76.8, 75.8, 53.0, 28.2, 24.9; IR (thin film): ν 3297, 2979, 2131,
1732, 1645, 1371 cm -1 ; ESI-HRMS calcd for C26H26N2O5Na m/z [M+23] + 469.1739; found
469.1749.
146
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