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Shiina et al.:
N-Benzylbenzamide (2). M.p. 104 °C. IR (KBr): 3 270, 1 643, 1 550. 1H NMR (CDCl3): 7.70 d,
2 H, J = 6.9 (ArH); 7.40–7.20 m , 8 H (ArH); 6.37 br s, 1 H (NH); 4.55 d, 2 H, J = 5.6 (Bn ).
13C NMR (CDCl3): 167.3 (CO); 138.2 (Ph ); 134.4 (Ph ); 131.5 (Ph ); 128.8 (Ph ); 128.6 (Ph );
127.9 (Ph ); 127.6 (Ph ); 126.9 (Ph ); 44.1 (Bn ).
N-Benzyl-2,2-dimethylpropanamide (3). M.p. 79 °C. IR (KBr): 3 278, 2 954, 1 651, 1 527.
1H NMR (CDCl3): 7.39–7.23 m , 5 H (ArH); 5.95 br s, 1 H (NH); 4.41 d, 2 H, J = 5.6 (Bn ); 1.14 s,
9 H (t-Bu). 13C NMR (CDCl3): 178.3 (CO); 138.5 (Ph ); 128.7 (Ph ); 127.6 (Ph ); 127.4 (Ph );
43.6 (Bn ); 38.7 (C in t-Bu); 27.6 (Me in t-Bu).
N-Benzyl-3-phenylpropanamide (4). M.p. 80 °C. IR (KBr): 3 286, 1 651, 1 535. 1H NMR
(CDCl3): 7.30–7.09 m , 10 H (ArH); 5.68 br s, 1 H (NH); 4.36 d, 2 H, J = 5.6 (Bn ); 2.96 t, 2 H,
J = 7.6 (CH2Ph ); 2.48 t, 2 H, J = 7.6 (CH2CO). 13C NMR (CDCl3): 171.8 (CO); 140.7 (Ph );
138.1 (Ph ); 128.6 (Ph ); 128.5 (Ph ); 128.4 (Ph ); 127.7 (Ph ); 127.4 (Ph ); 126.2 (Ph ); 43.5 (Bn );
38.4 (CH2CO); 31.7 (CH2Ph ).
(S)-3-Phenyl-N-1-phenylethylpropanamide ((–)-5, 98% ee). M.p. 92 °C. [α]2D1 –63.6 (c 1.03,
EtOH). IR (KBr): 3 278, 1 635, 1 558. 1H NMR (CDCl3): 7.21–7.00 m , 12 H (ArH); 5.90 br s,
1 H (NH); 4.97 quin , 1 H, J = 7.6 (CHN); 2.83 t, 2 H, J = 7.3 (CH2Ph ); 2.35 t, 2 H, J = 7.3
(CH2CO); 1.28 d, 3 H, J = 7.6 (Me). 13C NMR (CDCl3): 171.1 (CO); 143.1 (Ph ); 140.7 (Ph );
128.4 (Ph ); 128.4 (Ph ); 128.3 (Ph ); 127.1 (Ph ); 126.1 (Ph ); 126.0 (Ph ); 48.4 (CHN); 38.4
(CH2CO); 31.7 (CH2Ph ); 21.5 (Me). HPLC (CHIRALCEL OD, iPrOH–h exan e 1 : 14, flow rate
1.0 m l/m in ): tR = 18.8 m in ((+)-5), tR = 24.1 m in ((–)-5).
2-Phenyl-N-(3-phenylpropyl)propanamide ((±)-6). M.p. 93 °C. IR (KBr): 3 248, 1 643, 1 558,
756, 702. 1H NMR (CDCl3): 7.34–7.05 m , 10 H (ArH); 5.44 br s, 1 H (NH); 3.50 q, 1 H, J =
7.3 (CHCO); 3.24–3.15 m , 2 H (CH2N); 2.51 br t, 2 H (CH2Ph ); 1.76–1.69 m , 2 H (CH2); 1.50
d, 3 H, J = 7.3 (Me). 13C NMR (CDCl3): 174.1 (CO); 141.4 (Ph ); 141.3 (Ph ); 128.8 (Ph ); 128.3
(Ph ); 128.2 (Ph ); 127.5 (Ph ); 127.2 (Ph ); 125.9 (Ph ); 47.0 (CHCO); 39.1 (CH2N); 33.0
(CH2Ph ); 31.0 (CH2); 18.4 (Me). HR MS: calculated for C18H21NONa [M + Na]+ 290.1521,
foun d 290.1495.
N-(Diphenylmethyl)-2-phenylpropanamide ((±)-7). M.p. 134 °C. IR (KBr): 3 278, 1 643.
1H NMR (CDCl3): 7.37–6.95 m , 15 H (ArH); 6.19–6.00 m , 2 H (CHNH); 3.59 q, 1 H, J = 7.1
(CHCO); 1.48 d, 3 H, J = 7.1 (Me). 13C NMR (CDCl3): 173.1 (CO); 141.5 (Ph ); 141.3 (Ph );
141.2 (Ph ); 128.8 (Ph ); 128.5 (Ph ); 128.3 (Ph ); 127.5 (Ph ); 127.4 (Ph ); 127.3 (Ph ); 127.2 (Ph );
127.1 (Ph ); 127.0 (Ph ); 56.7 (CHN); 46.8 (CHCO); 18.3 (Me). HR MS: calculated for
C
22H21NONa [M + Na]+ 338.1521, foun d 338.1528.
(2R*)-2-Phenyl-N-((1S*)-1-phenylethyl)propanamide ((±)-8a). M.p. 127 °C. IR (KBr): 3 348,
1 643, 1 535. 1H NMR (CDCl3): 7.37–7.19 m , 10 H (ArH); 5.56 br d, 1 H (NH); 5.09 quin ,
1 H, J = 6.9 (CHN); 3.53 q, 1 H, J = 7.1 (CHCO); 1.51 d, 3 H, J = 7.1 (Me in acyl group); 1.34 d,
3 H, J = 6.9 (Me in am in o group). 13C NMR (CDCl3): 173.2 (CO); 143.2 (Ph ); 141.4 (Ph );
128.9 (Ph ); 128.6 (Ph ); 127.6 (Ph ); 127.2 (Ph ); 127.2 (Ph ); 126.0 (Ph ); 48.7 (CHN); 47.1
(CHCO); 21.5 (Me in am in o group); 18.6 (Me in acyl group). HR MS: calculated for
C
17H19NONa [M + Na]+ 276.1365, foun d 276.1374.
(2R*)-2-Phenyl-N-((1R*)-1-phenylethyl)propanamide ((±)-8b). M.p. 127 °C. IR (KBr): 3 237,
1 643, 1 542. 1H NMR (CDCl3): 7.34–7.17 m , 8 H (ArH); 7.08 dd, 2 H, J = 7.7, J′ = 1.2 (ArH);
5.59 d, 1 H, J = 7.1 (NH); 5.08 quin , 1 H, J = 7.1 (CHN); 3.57 q, 1 H, 7.3 (CHCO); 1.51 d,
3 H, J = 7.3 (Me in acyl group); 1.39 d, 3 H, J = 7.1 (Me in am in o group). 13C NMR (CDCl3):
173.1 (CO); 143.2 (Ph ); 141.3 (Ph ); 128.8 (Ph ); 128.5 (Ph ); 127.6 (Ph ); 127.2 (Ph ); 127.1 (Ph );
125.7 (Ph ); 48.6 (CHN); 47.1 (CHCO); 21.9 (Me in th e am in o group); 18.4 (Me in th e acyl
group). HR MS: calculated for C17H19NONa [M + Na]+ 276.1365, foun d 276.1320.
Collect. Czech. Chem. Commun. (Vol. 65) (2000)