ChemicalBook CAS DataBase List Fluticasone propionate

Fluticasone propionate synthesis

8synthesis methods

Product Name:Fluticasone propionate
CAS Number:80474-14-2
Molecular formula:C25H31F3O5S
Molecular Weight:500.57

Fluticasone propionate, synthesized by Glaxo Wellcome and launched in 1993, is a trifluorinated glucocorticosteroid. It shows good topical antiinflammatory activity and is commonly used as a safe and effective inhaled treatment for asthma and allergic rhinitis.
synthesis of fluticasone propionate

Fluticasone propionate can be synthesized from 9 by using BrCH2F,2a ClCH2F,5a or S-(monofluoromethyl) diarylsulfonium tetrafluoroborate 5f,g directly. Using BrCH2F can get an ideal yield; however, BrCH2F is costly and will destroy to the ozone layer. In addition, 9 reacted with BrCH2Cl or Br2CH2 and then by an anion exchange with AgF,2c,5e KF, or tetrabutylammonium fluoride5b to afford 1 in a low yield.
Improved Synthesis of Fluticasone Propionate

373-52-4 Synthesis

373-52-4
131 suppliers
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80474-45-9 Synthesis

80474-45-9
108 suppliers
$501.81/5MG

80474-14-2
615 suppliers
$19.80/5mg

Yield:80474-14-2 91.7%

Reaction Conditions:

with potassium hydrogencarbonate in N,N-dimethyl-formamide at -10 - 20; for 2 h;

Steps:

1-11 Substitution into ester reaction:

In a four-necked bottle, add 31.7g IM4 and 159ml dimethylformamide, lower the temperature to below 20 , add 7.2g potassium bicarbonate,Then lower the temperature to below -10 ,Add 8.7g of fluorobromomethane dropwise,Then control the temperature -10-20 for 2 hours, after the IM4 reaction is detected by HPLC, add 1mol / L hydrochloric acid dropwise, adjust the PH value to 2, crystallize, filter, wash and dry to obtain 32.5g crude fluticasone propionate, this step The molar yield is 96.3%.Refining reaction: In a four-necked bottle, add 31.2g crude fluticasone propionate and 437ml acetone, raise the temperature to 55 , stir to dissolve, control the temperature 50-60 , add 250ml of purified water dropwise, then slowly lower the temperature Crystallization below 15 , filtration, washing and drying to obtain 28.6g crude fluticasone propionate, the molar yield of this step is 91.7%.

References:

CN110698530,2020,A Location in patent:Page/Page column 7-15

Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(hydroxymethyl) ester, (6α,11β,16α)-

709002-83-5
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80474-14-2
615 suppliers
$19.80/5mg

References

80474-67-5 Synthesis

5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate

80474-67-5
23 suppliers
$345.00/25mg

80474-14-2
615 suppliers
$19.80/5mg

References

373-53-5 Synthesis

373-53-5
59 suppliers
$165.00/1g

80474-45-9 Synthesis

80474-45-9
108 suppliers
$501.81/5MG

80474-14-2
615 suppliers
$19.80/5mg

References

Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-16-methyl-3-oxo-17-(1-oxopropoxy)-11-[(2,2,2-trifluoroacetyl)oxy]-, S-(fluoromethyl) ester, (6α,11β,16α,17α)-

1414857-56-9
0 suppliers
inquiry

80474-14-2
615 suppliers
$19.80/5mg

References

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