Latanoprost
isopropyl-(Z)7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate.
130209-82-4
XA41, PhXA34 [as 15 (R, S) -isomer], PhXA41, Xalatan
(Zanoni, G. et al., Tetrahedron 2010, 66, 7472)
SYNTHESIShttp://newdrugapprovals.org/2014/08/02/latanoprost/
http://www.google.com/patents/WO2013186550A1?cl=en
latanoprost 77 (71 mg, 64 %) as a clear colourless oil. The IR, 13C, and optical rotation data were consistent with the literature (Zanoni, G. et al., Tetrahedron 2010, 66, 7472). Rf = 0.44 (EtOAc)
vmax (neatVcm“1 3360 (broad), 2980, 2931, 2857, 1712, 1495, 1454, 1374, 1311, 1247, 1180, 1106, 1030, 966, 910, 820, 731, 699
*H NMR (400 MHz; CDCI3) δΗ = 1.23 (6 H, d, J = 6.4 Hz, 2 x CH3), 1.30-1.90, (14 H, m, 5 x CH2, 2 x CH, 2 x OH), 2.07-2.39 (6 H, m, 3 x CH2), 2.45 (1 H, d, J = 5.5 Hz, OH), 2.63- 2.86 (2 H, m, CH2), 3.68 (1 H, br.s, CHO ), 3.95 (1 H, br.s, CHOH), 4.18 (1 H, br.s, CHO ), 5.01 (1 H, sept., J = 6.4 Hz, OCH(CH3)2), 5.35-5.52 (2 H, m, 2 x =CH), 7.16-7.24 (3 H, m, ArH’s), 7.25-7.32 (2 H, m, ArH’s)
13C NMR (125 MHz; CDCI3) 5C = 21.9 (2 x CH3), 24.9 (CH2), 26.6 (CH2), 26.8 (CH2), 29.6 (CH2), 32.1 (CH2), 34.0 (CH2), 35.7 (CH2), 39.0 (CH2), 42.5 (CH2), 51.8 (CH), 52.7 (CH), 67.6 (OCH), 71.2 (OCH), 74.5 (OCH), 78.6 (OCH), 125.7 (CH), 128.3 (2 x ArCH), 128.3 (2 x ArCH), 129.3 (CH), 129.5 (CH), 141.1 (ArC), 173.5 (C=0)
[a]D 23 33.0 (c. 1.0, MeCN) (lit, [a]D 20 32.7 (c. 1.0, MeCN))
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