Quinapril benzyl ester maleate synthesis
- Product Name:Quinapril benzyl ester maleate
- CAS Number:82586-54-7
- Molecular formula:C36H40N2O9
- Molecular Weight:644.71
![Benzenebutanoicacid,-[[(1S)-1-carboxyethyl]amino]-,monoethylester,hydrochloride,(S)-(9CI)](/CAS/GIF/80828-26-8.gif)
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Yield:-
Reaction Conditions:
Stage #1: benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid saltwith triethylamine in dichloromethane at 0 - 5; for 0.166667 h;
Stage #2: N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride in dichloromethane at -20 - 25; for 1 h;
Steps:
1
35.4gms (0.086 moles) of the para-toluene sulfonate salt of the benzyl ester of (S)- 1, 2,3, 4-tetrahydro-isoquinoline-3-carboxylic acid (IV) was dissolved in 150ML dichloromethane. 29ms (0.287 moles) of triethyl amine was added at 0-5 C and the reaction mixture stirred at 0-5 C for 10MINUTES. A solution of the acid chloride of compound (III) prepared in the earlier step in 150ML of dichloromethane was added at-15 TO-20 C to the reaction mixture. The reaction mixture was then stirred at 20-25 C for LHOUR. The organic phase was separated and washed with 200ML of hydrochloric acid followed by 200ML of water. The organic phase was then concentrated under vacuum. The residue of the quinapril benzyl ester was dissolved in 130ML ethyl acetate and washed with 200ML of 10% aqueous sodium bicarbonate solution followed by water wash (200ML).
References:
WO2004/54980,2004,A1 Location in patent:Page 23;13;16
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