17-Hydroxy-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-,(7α,17β) estr-4-en-3-one synthesis
- Product Name:17-Hydroxy-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-,(7α,17β) estr-4-en-3-one
- CAS Number:1334316-46-9
- Molecular formula:C32H49F5O3S
- Molecular Weight:608.79
![Estr-4-en-3-one, 17-(acetyloxy)-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-, (7α,17β)-](/CAS/20210305/GIF/1334316-50-5.gif)
1334316-50-5
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Yield:1334316-46-9 83%
Reaction Conditions:
with water;sodium hydroxide in methanol at 20; for 4 h;
Steps:
(7α,17β)-17-Hydroxy-7-{9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl}estr-4-en-3-one (6a)
Aqueous NaOH (10M, 6.6 mL, 66 mmol) was added to a stirred solution of 5a (17.2 g, 26.5 mmol) in MeOH (120 mL). After 4 h the solution was concentrated, diluted with water (1 L) and extracted with EtOAc (2 x 500 mL). The extracts were washed with saturated brine, dried (MgSO4) and evaporated. The residue was purified by MPLC, eluting with 1% MeOH/EtOAc. The appropriate fractions were combined and concentrated to give an oil which crystallised on standing. Trituration with hexane gave 6a (13.3 g, 83%) as a white free flowing powder. 1H NMR (500 MHz, CDCl3) δ 0.79 (3H, s), 0.90-1.61 (24H, m), 1.64-1.83 (4H, m), 1.84-1.93 (1H, m), 1.97-2.31 (9H, m), 2.35-2.42 (1H, m), 2.48 (1H, dd), 2.58-2.77 (4H, m), 3.63-3.68 (1H, m), 5.80 (1H, s); LCMS m/z = 609.63 [M+H]+, RT = 1.89 (acidic gradient), 100% purity.
References:
Bradbury, Robert H.;Hales, Neil J.;Rabow, Alfred A.;Walker, Graeme E.;Acton, David G.;Andrews, David M.;Ballard, Peter;Brooks, Nigel A.N.;Colclough, Nicola;Girdwood, Alan;Hancox, Urs J.;Jones, Owen;Jude, David;Loddick, Sarah A.;Mortlock, Andrew A. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 18,p. 5442 - 5445] Location in patent:supporting information; experimental part
![1-BROMO-9-[(4,4,5,5,5-PENTAFLUOROPENTYL)THIO]-NONANE](/CAS/GIF/148757-89-5.gif)
148757-89-5
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![(7alpha,17beta)-17-(Acetyloxy)-7-[9-[(4,4,5,5,5-pentafluoropentyl)thio]nonyl]estr-4-en-3-one](/CAS/20150408/GIF/415927-29-6.gif)
415927-29-6
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2590-41-2
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$50.00/1g
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