BIMATOPROST
155206-00-1
Lumigan, Latisse, AGN 192024, bimatoprostum, UNII-QXS94885MZ, Lumigan (TN), CHEBI:51230, AC1NSJUW, AGN-192024
Molecular Formula: C25H37NO4
Molecular Weight: 415.56558
(Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010); Gutman, A. et al., US 20090163596 (2009)).
SYN
http://newdrugapprovals.org/2014/07/31/bimatoprost/
http://www.google.com/patents/EP2454227A1?cl=en
BIMATOPROST97 (82.6 mg, 41% over 2 steps) as a clear, colourless oil. Analytical data consistent with the literature (Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010); Gutman, A. et al., US 20090163596 (2009)).
max (filmVcm-1 3300 (broad), 2930, 1643, 1550, 1453, 1332, 1293, 1048, 1029, 968, 729, 698
*H NMR (400 MHz; CDCI3) δΗ = 1.09 (t, J = 7.1 Hz, 3H, CH3), 1.42-2.40 (m, 14H, 6 x CH2, 2 x CH), 2.67 (m, 2H, CH2), 3.22 (dq, J = 7.1, 6.3 Hz, 2H, CH2NH), 3.41 (broad s, 3H, 3 x OH), 3.80-4.30 (broad m, 3H, 3 x CHOH), 5.37 (m, 2H, 2 x =CH), 5.47 (dd, J = 15.2, 7.9 Hz, 1H, =CH), 5.59 (dd, J = 15.2, 7.9 Hz, 1H, =CH), 5.90 (broad s, 1H, NH), 7.17 (m, 3H, ArCH’s), 7.26 (m, 2H, ArCH’s)
13C NMR ( 100 MHz; CDCI3) 5C = 14.8 (CH3), 25.4 (CH2), 25.6 (CH2), 26.7 (CH2), 31.9 (CH2), 34.4 (CH2NH), 35.8 (CH2C=0), 38.8 (CH2), 42.9 (CH2), 50.2 (CH), 55.5 (CH), 72.3 (CHOH), 72.4 (CHOH), 77.7 (CHOH), 125.8 (ArCH), 128.4 (2 x ArCH), 128.5 (2 x ArCH), 129.1 (=CH), 129.7 (=CH), 133.7 (=CH), 135.1 (=CH), 142.0 (ArC), 173.4 (C=0)
m/z (ESI+) 438.2 [MNa]+
HRMS (ESI+) calcd for Q^IV^Na [MNa]+ 438.2614, found 438.2615
[a]D 22 +41.1 (c. 0.35, CH2CI2) (lit. – Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010), +32.7 (c. 0.33, CH2CI2)) (lit. – Gutman, A. et al., US 20090163596 (2009), +36 (c. 1, MeOH))
