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35–40 °C. The reaction mixture was stirred until a clear solution
was obtained. The EtOH was evaporated under vacuum and the
residue was washed successively with H2O (2 mL) and hexane or
petroleum ether (2 mL) to afford almost pure N-Boc amino acids
or N-Boc peptides. If necessary, the crude products were
recrystallized.
7. (a) Darnbrough, S.; Mervic, M.; Condon, S. M.; Burns, C. J. Synth. Commun. 2001,
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All the products were characterized by mp, 1H and 13C NMR
spectroscopy, microanalysis and by comparison with authentic
samples reported in the literature.
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3.1. N-(tert-Butoxycarbonyl)-2-amino-3-hydroxypyridine (Table
1, entry 24)
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Off-white solid, yield: 95%; mp: 129–132 °C; 1H NMR (300 MHz,
CDCl3): d = 1.54 (s, 9H), 7.00 (dd, J = 8, 4.7 Hz, 1H), 7.32 (dd, J = 8,
1.5 Hz, 1H), 7.91 (dd, J = 4.7, 1.5 Hz, 1H), 9.31 (s, 1H, OH), 9.96
(br s, 1H, NH); 13C NMR (75 MHz, CDCl3): d = 28.2 (CH3), 83.1 (C),
121.2 (CH), 127.8 (CH), 138.8 (CH), 140.3 (C), 143.8 (C), 156.1
(C@O); Anal. Calcd for C10H14N2O3: C, 57.13; H, 6.71; N, 13.32.
Found: C, 56.33; H, 6.64; N, 13.20.
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3.2. N-Boc-L-proline (Table 2, entry 3)
White solid, yield: 98%; mp: 137 °C; 1H NMR (300 MHz, CDCl3):
(1:0.9 rotamer ratio, the asterisk denotes minor rotamer peaks),
d = 1.40 (s, 9H), 1.45⁄ (s, 9H), 1.85–2.00 (m, 4H), 2.04–2.25 (m,
4H), 3.31–3.55 (m, 4H), 4.22 (m, 1H), 4.33⁄ (m, 1H), 11.31 (br s,
2H, CO2H); 13C NMR (75 MHz, CDCl3): d = 23.6 (CH2), 24.3⁄ (CH2),
28.2 (CH3), 28.4⁄ (CH3), 29.0⁄ (CH2), 30.8 (CH2), 46.3 (CH2), 46.9⁄
(CH2), 58.9 (CH), 80.3 (C), 81.0⁄ (C), 153.9 (C@O), 155.9⁄ (C@O),
176.2⁄ (CO2H), 178.9 (CO2H).
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Acknowledgement
The authors are thankful to the University of Mazandaran re-
search council for partial financial support.
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Supplementary data
Experimental procedures, analytical and spectral characteriza-
tion details, comparison tables, copies of 1H and 13C NMR spectra
of compounds in Table 1 (entries 2, 3, 6, 7, 10, 12–14, 16, 17, 23,
24, 27, 30 and 33–39) and Table 2 (entries 1–4, 7–12 and 15) are
provided. Supplementary data associated with this article can be
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