75847-73-3 Usage
Uses
Different sources of media describe the Uses of 75847-73-3 differently. You can refer to the following data:
1. angiotensin converting enzyme inhibitor
2. It is used for hypertension and chronic cardiac insufficiency.
3. Enalapril is used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure. It has been proven to protect the function of the kidneys in hypertension, heart failure, and diabetes, and may be used in the absence of hypertension for its kidney protective effects. It is widely used in chronic kidney failure.
Definition
ChEBI: A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).
Mechanism of action
Like captopril, enalapril selectively suppresses the rennin–angiotensin–aldosterone system,
inhibits angiotensin-converting enzyme, and prevents conversion of angiotensin I into
angiotensin II.
Synthesis
Enalapril, (S)-1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline
(22.7.12), is synthesized by reacting the benzyl ester of L-alanyl-L-proline with the ethyl
ester of 3-benzoylacrylic acid, which forms the product 22.7.11, the reduction of which
with hydrogen using a Raney nickel catalyst removes the protective benzyl group, giving
the desired enalapril (22.7.12) [24]. Alternative methods of syntheses have also been proposed.
Check Digit Verification of cas no
The CAS Registry Mumber 75847-73-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,8,4 and 7 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 75847-73:
(7*7)+(6*5)+(5*8)+(4*4)+(3*7)+(2*7)+(1*3)=173
173 % 10 = 3
So 75847-73-3 is a valid CAS Registry Number.
InChI:InChI=1/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
75847-73-3Relevant articles and documents
Hydrogenation N-alkylation of α-alanyl-α-proline with ethyl 2-oxo-4-phenylbutanoate on organometallic catalysts
Abdullaev, M. G.
, (2020)
New nickel- and palladium-containing catalysts for reductive N-alkylation of α-alanyl-α-proline dipeptide with ethyl 2-oxo-4-phenylbutanoate have been investigated. Based on the empirical data obtained, the optimal scheme for the catalytic synthesis of en
Improved stereoselectivity in the heterogeneous catalytic synthesis of enalapril obtained through multidimensional screening
Huffman, Mark A.,Reider, Paul J.
, p. 831 - 834 (1999)
A multidimensional screening of catalysts and additives led to the discovery of improved conditions for the diastereoselective reductive amination which produces enalapril. Additives acetic acid and potassium fluoride, which in isolation are detrimental, work together to improve the SSS: RSS selectivity with Ra-Ni in ethanol to 17: 1 from 11: 1.
PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE
-
, (2015/01/07)
A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.
