NOESY experiment of diastereomer 10α (3S, 5R)
(3S,5R)-3-Benzyl-5-isobutyl-1,3,4,5-tetrahydro-2H-thieno[3,2-e]- [1,4]diazepin-2-one (10α):
Pale yellow solid, 50% (64.0 mg),
m.p. 66.7–67.4 °C.
[α]D 29 = –122.2 (c = 1.0, MeOH).
1 H NMR (CDCl3, 300 MHz): δ = 0.90 (d, J = 6.3 Hz, 3 H), 0.92 (d, J = 6.6 Hz, 3 H), 1.36–1.54 (m, 2 H), 1.81 (m, 1 H), 2.08 (s, 1 H), 3.13 (d, J = 5.1 Hz, 2 H), 3.93 (t, J = 5.1 Hz, 1 H), 4.67 (dd, J = 3.0, J = 9.9 Hz, 1 H), 7.15–7.30 (m, 8 H) ppm.
13C NMR (CDCl3, 75 MHz): δ = 21.48, 23.79, 24.71, 36.81, 42.09, 59.63, 73.76, 111.68, 120.97, 125.09, 126.92, 126.97, 128.70, 129.83 (2 C), 135.11, 136.90, 172.65 ppm.
LC–MS (ESI+): m/z = 315.2 [M + H]+.
HRMS: calcd. for C18H23N2OS 315.1531 [M + H]+; found 315.1531
10.1002/ejoc.201500943
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