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3
165.2 (d, JCP = 2.1 Hz, C O amide). 31P NMR: δ 19.0. Anal. Calcd. for C18H28NO6P
(385.40): C 56.10, H 7.32, N 3.63, found: C 55.89, H 7.16, N 3.78%.
1-(N-tert-Butylcarbamoyl)-1-(diethoxyphosphoryl)ethyl 4-methylbenz-
oate (8c). Colorless viscous oil, yield: 70%. IR (νmax, cm−1): 3436 (NH), 2922,
1732(C O), 1688(C O), 1524, 1455, 1268 (P O), 1027. 1H NMR: δ 1.28–1.42 (m, 6H,
2CH3CH2OPO), 1.32 (s, 9H, Me3C), 1.92 (d, 3H, 3JHP = 15.5 Hz, CH3), 2.42 (s, 3H, Me),
4.15–4.40 (m, 4H, 2CH2OPO), 6.24 (s, NH), 7.26 (d, 2 H, 3JHH = 8.0 Hz, arom), 7.93 (d,
2 H, 3JHH = 8.0 Hz, arom). 13C NMR: δ 16.4 (d, 3JCP = 5.7 Hz, CH3CH2OPO), 16.5 (d,
2
3JCP = 5.7 Hz, CH3CH2OPO), 17.8 (d, JCP = 2.5 Hz, CH3), 21.7 (Me), 30.9 (Me3C),
51.6 (Me3C), 63.9 (d, 2JCP = 5.7 Hz, CH2OPO), 64.0 (d, 2JCP = 6.3 Hz, CH2OPO), 80.8
(d, 1JCP = 160.4 Hz, C), 126.9, 129.2, 129.9, 144.3, 164.1 (d, 3JCP = 12.8 Hz, C O ester),
2
165.3 (d, JCP = 2.1 Hz, C O amide). 31P NMR: δ 19.1. Anal. Calcd. for C19H30NO6P
(399.43): C 57.13, H 7.57, N 3.51, found C 57.46, H 7.76, N 3.74%.
1-(N-tert-Butylcarbamoyl)-1-(diethoxyphosphoryl)ethyl 4-chlorobenzo-
ate (8d). Colorless viscous oil, yield: 71%. IR (νmax, cm−1): 3393(NH), 2978,
1738(C O), 1698(C O), 1526, 1454, 1262 (P O), 1016, 757. 1H NMR: δ 1.30–1.45 (m,
6H, 2CH3CH2OPO), 1.31 (s, 9H, Me3C), 1.91 (d, 3H, 3JHP = 15.5 Hz, CH3), 4.19- 4.40
(m, 4H, 2CH2OPO), 6.28 (s, NH), 7.42 (d, 2 H, 3JHH = 7.6 Hz, arom), 7.96 (d, 2 H, 3JHH
= 7.6 Hz, arom). 13C NMR: δ 16.4 (d, 3JCP = 5.7 Hz, CH3CH2OPO), 16.5 (d, 3JCP = 5.7
Hz, CH3CH2OPO), 18.1 (d, 2JCP = 2.5 Hz, CH3), 28.5 (Me3C), 51.7 (Me3C), 64.0 (d, 2JCP
2
1
= 5.4 Hz, CH2OPO), 64.1 (d, JCP = 5.4 Hz, CH2OPO), 81.0 (d, JCP = 157.2 Hz, C),
128.1, 128.9, 131.2, 140.0, 163.6 (C O), 165.0 (C O). 31P NMR: δ 18.9. Anal. Calcd.
for C18H27NO6PCl (419.85): C 51.49, H 6.48, N 3.33, found C 51.56, H 6.61, N 3.50%.
1-(N-Cyclohexylcarbamoyl)-1-(diethoxyphosphoryl)-1-phenylmethyl
benzoate (8e). Pale yellow viscous oil, yield: 57%. IR (νmax, cm−1): 3306(NH), 2931,
1742(C O), 1692(C O), 1540, 1450, 1266 (P O), 1031. 1H NMR: δ 1.10 (t, 3H, 3JHH
=
3
7.0 Hz, CH3CH2OPO), 1.24 (t, 3H, JHH = 7.2 Hz, CH3CH2OPO), 1.21–1.94 (m, 10H,
cyclohexyl), 3.78 (m, 1H, CHN), 3.93 (m, 2H, CH2OPO), 4.21 (m, 2H, CH2OPO), 7.31-
3
3
7.63 (m, 7H, NH and arom), 7.74 (d, 2H, JHH = 6.5 Hz, arom), 8.16 (d, 2 H, JHH
=
8.0 Hz, arom). 13C NMR: δ 16.1 (d, 3JCP = 5.7 Hz, CH3CH2O), 16.3 (d, JCP = 6.3 Hz,
3
2
CH3CH2OPO), 18.1 (d, JCP = 2.5 Hz, CH3), 24.5, 24.6, 25.4, 32.4, 32.6, 48.5 (CHN),
2
2
1
64.3 (d, JCP = 7.5 Hz, CH2OPO), 64.7 (d, JCP = 6.9 Hz, CH2OPO), 83.2 (d, JCP
=
153.5 Hz, C), 126.3 (d, JCP = 4.4 Hz, arom), 128.2 (d, JCP = 2.5 Hz, arom), 128.3 (d,
JCP = 2.5 Hz, arom), 128.6, 129.8, 130.0, 133.5, 134.3 (d, JCP = 3.8 Hz, arom), 164.0
(d, 3JCP = 6.3 Hz, C O ester), 164.3 (d, 2JCP = 5.7 Hz, C O amide). 31P NMR: δ 16.3.
Anal. Calcd. for C25H32NO6P (473.51): C 63.41, H 6.81, N 2.96, found C 63.55, H 6.95,
N 3.11%.
1-(N-tert-Butylcarbamoyl)-1-(diethoxyphosphoryl)-1-phenylmethyl ben-
zoate (8f). Pale yellow viscous oil, yield: 52%. IR (νmax, cm−1): 3428(NH); 2976;
1742(C O); 1697(C O); 1550; 1451; 1268 (P O); 1025. 1H NMR: δ 1.13 (t, 3H, 3JHH
= 7.0 Hz, CH3CH2OPO); 1.25 (t, 3H, 3JHH = 6.8 Hz, CH3CH2OPO); 1.39 (s, 9H, Me3C);
4.10 (m, 2H, CH2OPO); 4.20 (m, 2H, CH2OPO); 7.26–7.63 (m, 7H, NH and arom); 7.73
(d, 2H, 3JHH = 7.5 Hz, arom); 8.17 (d, 2 H, 3JHH = 7.2 Hz, arom). 13C NMR: δ 16.2 (d,
3JCP = 6.3 Hz, CH3CH2OPO); 16.3 (d, 3JCP = 5.7 Hz, CH3CH2OPO); 28.5 (Me3C); 51.9
2
2
(Me3C); 64.3 (d, JCP = 7.5 Hz, CH2OPO); 64.6 (d, JCP = 6.3 Hz, CH2OPO); 81.1 (d,
1JCP = 154.7 Hz, C); 126.5 (d, JCP = 4.4 Hz, arom); 128.2 (d, JCP = 4.1 Hz, arom); 128.3
(d, JCP = 5.0 Hz, arom); 128.6; 129.8; 130.0; 133.5; 134.2 (d, JCP = 3.6 Hz, arom); 163.9