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publication. The authors only mentioned the recovery of
lactone 14 in 15% yield, after treatment of b-(4-azidophe-
nyl)-propanoic acid with TFA at 0 ꢁC (catalysis with
trifluoromethane sulfonic acid), then with TFAA, before
aqueous work-up. No isomer 16 was detected, and much
tar was formed. In fact, from our experiments, it appears
that both regioisomers 14 and 16 are formed, but that 14 is
more soluble in water than 16. After aqueous basic work-
up, only 16 could be extracted with an organic solvent.
21. Rearrangement of 3-(4-azidophenyl)-propionic acid. Acid 9
(275 mg) was added by small portions, during 5 h, to cold
(0 ꢁC) trifluoroacetic acid (13.5 mL), under stirring, in
argon atmosphere. After a further 2 h at 0 ꢁC, trifluoro-
acetic anhydride (3.8 mL) was added and the mixture was
kept at room temperature overnight. After concentration
under vacuum, the residue was dissolved in ethyl acetate
(15 mL), washed with 1 M Na2CO3, water and brine (three
times), dried over MgSO4 and concentrated. Column
chromatography on silica gel (elution with CH2Cl2) gave
6-trifluoroacetamido-3,4-dihydrocoumarin (16) as a white
solid (260 mg, 40% yield): mp 130 ꢁC; RF = 0.4 (CH2Cl2/
CH3CN, 19:1); IR m = 1755, 1716 cmꢀ1; MS (APCI) m/
z = 260 (100%, C11H8O3NF3 + 1); 1H NMR (CD3OD,
500 MHz, 50 ꢁC) d = 7.31 (d, J = 2.4 Hz, 1H), 7.29 (dd,
J = 8.55 and 2.4 Hz, 1H), 6.79 (d, J = 8.55 Hz, 1H), 2.92
(m, 2H), 2.65 (m, 2H); 13C NMR (acetone-d6, 125 Hz)
d = 167.2, 154.5 (q, JC–F = 45 Hz), 149.4, 132.1, 124,
120.5, 120.4, 116.6, 115.8 (q, JC–F = 287 Hz), 28.2, 23.2.
22. Preparation of ester 17. Compound 16 (780 mg) was
dissolved in methanol (30 mL) and 6 N HCl (20 mL), and
refluxed for 20 h. After evaporation under vacuum, the
residue was dissolved in methanol (20 mL), concentrated
H3PO4 (3 drops) was added and the solution was refluxed
for 12 h. After concentration, the residue was dissolved in
EtOAc and washed with aqueous HCl (pH 1). The
aqueous phase was separated, treated with Na2CO3 to
reach pH 8 and extracted (three times) with EtOAc. The
organic phases were collected and dried over MgSO4.
Concentration under vacuum gave a beige solid which was
purified by precipitation from CH2Cl2, filtration and
washing with ether to yield 17 as a white powder
(294 mg, 50% yield): mp 131–133 ꢁC; RF = 0.57 (EtOAc);
IR m = 3350, 1724, 1167 cmꢀ1; MS (APCI) m/z = 196.0
(100%, C10H13O3N + 1); 1H NMR (CDCl3, 500 MHz)
d = 6.70 (d, J = 8.2 Hz, 1H), 6.48 (dd, J = 2.9 and 8.2 Hz,
1H), 6.46 (d, J = 2.9 Hz, 1H), 3.67 (s, 3H), 2.82 (t,
J = 6.7 Hz, 2H), 2.69 (t, J = 6.7 Hz, 2H); 13C NMR
(CDCl3, 125 MHz) d = 175.7, 146.9, 139.7, 128.1, 118.0,
117.2, 115.1, 52.0, 34.9, 24.5.
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25. Protocols of Scheme 4 are provided as Supplementary
Information. Structural characterization of B-c: 1H NMR
(acetone-d6, 300 MHz) d = 9.14 (br s, 1H, NH urea), 8.83
(br s, 1H, NH urea), 8.15 (m, 1H), 7.64 (m, 2H + NH
amide), 7.52 (m, 1H), 7.48 (d, J = 8.3 Hz, 2H), 7.37 (br s,
1H), 7.27 (m + d, J = 8.3 Hz, 1H + 2H), 6.85 (m, 1H), 4.11
(t, J = 5.2 Hz, 2H), 3.81 (t, J = 5.2 Hz, 2H), 3.64 (t,
J = 5.2 Hz, 2H), 3.58 (s + t, 2H
+
2H), 3.48 (t,
J = 5.2 Hz, 2H), 3.20 (m, 2H), 2.84 (t, J = 6.7 Hz, 2H),
2.57 (t, J = 6.7 Hz, 2H); 13C NMR (acetone-d6, 50 MHz)