ChemicalBook CAS DataBase List 17-Hydroxy-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-,(7α,17β) estr-4-en-3-one

17-Hydroxy-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-,(7α,17β) estr-4-en-3-one synthesis

4synthesis methods

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)-

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17-Hydroxy-7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-,(7α,17β) estr-4-en-3-one

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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

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References

(7alpha,17beta)-17-(Acetyloxy)-7-[9-[(4,4,5,5,5-pentafluoropentyl)thio]nonyl]estr-4-en-3-one

415927-29-6
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References

2590-41-2 Synthesis

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