A kind of method of synthesizing tafluprost
A compound, selected technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc.
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Embodiment 1
[0048] (Z)-7-((1R,2R,3R,5S)-5-Acetoxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)- Isopropyl 3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate 2.
[0049] 2.6 g of dimethyl 2-oxo-3-phenoxypropylphosphonate 7 was dissolved in 30 ml of toluene, and 0.42 g of LiOH.H 2 O, 0.05 g of tetrabutylammonium bromide, stirred at -20°C for 1 hour. Added 5 g of (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3 -((Tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acid isopropyl ester 1 and 60 ml of toluene mixed solution, continue to stir for 24 hours, TLC detects that raw material 7 remains , the reaction solution was washed twice with brine, dried over anhydrous sodium sulfate, and concentrated to obtain 4.4 g of a light yellow liquid of 2. The yield was 78.5%. It was directly used in subsequent reactions. A small sample was purified by silica gel, ethyl acetate / n-hexane (1:2) was eluted to obtain 2 as a yellow liquid. 1 H-NMR (CDCl 3 ,300MHz)δ(ppm):1.23(d,6H),1.45-2.05(m,13H),2.07(s,3H),...
Embodiment 2
[0051] (Z)-7-((1R,2R,3R,5S)-5-Acetoxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)- Isopropyl 3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate 2.
[0052]Dissolve 3.6 g of dimethyl 2-oxo-3-phenoxypropylphosphonate 7 in 30 ml of dichloromethane, add 0.58 g of butyllithium, 0.05 g of tetrabutylammonium bromide, room temperature (20-30°C ) and stirred for 1 hour. Added 5 g of (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2- base)oxy)cyclopentyl)hept-5-enoic acid isopropyl ester 1 and 60 ml of dichloromethane mixed solution, continue to stir at room temperature for 15 hours, TLC detects that there is no residue of raw material 1, and the reaction solution is washed twice with brine , dried over anhydrous sodium sulfate, and concentrated to obtain 5.6 g of a light yellow liquid of 2. The yield was 85.4%. It was directly used in subsequent reactions.
Embodiment 3
[0054] (Z)-7-((1R,2R,3R,5S)-5-Acetoxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)- Isopropyl 3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate 2.
[0055] 6.1 g of 2-oxo-3-phenoxypropyl phosphonic acid dimethyl ester 7 was dissolved in 45 ml of tetrahydrofuran, added 1.0 g of t-BuOK, 0.05 g of tetrabutylammonium bromide, and stirred at 80°C for 1 hour. Added 5 Gram (Z)-7-((1R,2R,3R,5S)-5-acetoxy-2-formyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentene base) Hept-5-enoic acid isopropyl ester 1 and 60 ml of tetrahydrofuran mixed solution, continue to stir for 1 hour, TLC detects that there is no raw material 1 residue, the reaction solution is poured into 200 ml of brine, extracted with 50ml×4 ethyl acetate, combined The organic phase was washed twice with brine, dried over anhydrous sodium sulfate, and concentrated to obtain 4.9 g of a light yellow liquid of 2. The yield was 74.9%. It was directly used in subsequent reactions.
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