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Enalapril
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Name

Enalapril

 EINECS N/A
CAS No. 75847-73-3 Density 1.204 g/cm3
PSA 95.94000 LogP 1.93340
Solubility Soluble in water at 25mg/ml Melting Point 143-144.5oC
Formula C20H28N2O5 Boiling Point 582.4 °C at 760 mmHg
Molecular Weight 376.453 Flash Point 306 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 75847-73-3 (Enalapril) Hazard Symbols N/A
Synonyms

L-Proline,1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-, (S)-;

Article Data 16

Enalapril Synthetic route

89371-34-6

N-succinimidyl (2S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propionate

147-85-3

L-proline

75847-73-3

enalapril

Conditions
ConditionsYield
With triethylamine In ethanol; water for 16h; Ambient temperature;92.9%
108428-39-3

N--L-alanyl>-L-proline tert butyl ester

75847-73-3

enalapril

Conditions
ConditionsYield
With trifluoroacetic acid for 3h; Ambient temperature;85%
With hydrogenchloride In ethyl acetate
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

13485-59-1

L-alanyl-L-proline

75847-73-3

enalapril

Conditions
ConditionsYield
With hydrogen In ethanol at 45℃; under 735.074 - 772.577 Torr; Catalytic behavior; Kinetics; Solvent; Reagent/catalyst;70%
13485-59-1

L-alanyl-L-proline

17451-20-6, 55674-14-1, 55629-96-4

(E)-ethyl-2-oxo-4-phenylbut-3-enoate

75847-73-3

enalapril

Conditions
ConditionsYield
With 4 A molecular sieve; hydrogen; triethylamine; palladium In ethanol at 20℃; for 44h;65%
64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

13485-59-1

L-alanyl-L-proline

A

75847-73-3

enalapril

B

76420-74-1

enalapril

Conditions
ConditionsYield
nickel Product distribution; var. catalysts and reducing agents, diastereomeric ratio;
With 3 A molecular sieve; hydrogen; nickel In ethanol at 23 - 28℃; under 2068.6 Torr; for 18h; Title compound not separated from byproducts;
With potassium fluoride; 3 A molecular sieve; hydrogen; acetic acid; nickel In ethanol at 22℃; under 760 Torr; for 18h; Yield given; Yields of byproduct given;
120924-94-9

N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester

75847-73-3

enalapril

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 735.5 Torr; for 2h; Ambient temperature; Yield given;
With palladium 10% on activated carbon; hydrogen In methanol at 15 - 20℃;
147-85-3

L-proline

406213-94-3

C18H26N2O4

75847-73-3

enalapril

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 20℃; for 8h;
82717-96-2

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

75847-73-3

enalapril

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: HCl / CH2Cl2; dioxane / -5 - 0 °C
1.2: ClCOCOCl / dimethylformamide; CH2Cl2; dioxane / -5 - 0 °C
2.1: dimethylformamide; CH2Cl2; dioxane / 1 h / 20 °C
3.1: DBU / acetonitrile; CH2Cl2 / 8 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 86 percent / NaHCO3, diphenylchlorophosphate / acetone / 1 h / 50 °C
2: 92.9 percent / Et3N / ethanol; H2O / 16 h / Ambient temperature
View Scheme
103377-40-8

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine acid chloride

75847-73-3

enalapril

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide; CH2Cl2; dioxane / 1 h / 20 °C
2: DBU / acetonitrile; CH2Cl2 / 8 h / 20 °C
View Scheme
104-53-0

3-phenyl-propionaldehyde

sodium-

sodium-

75847-73-3

enalapril

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 45 percent / methanol; H2O / 8 h / 70 °C
2: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9
3: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h
4: 95 percent / SOCl2 / 24 h / Ambient temperature
5: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C
6: 85 percent / TFA / 3 h / Ambient temperature
View Scheme

Enalapril Chemical Properties

 
IUPAC Name:  (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid 
Molecular Formula: C20H28N2O5
Molecular Weight: 376.45 g/mol
Product Categories: Angiotensin
Classification Code: Angiotensin-converting enzyme inhibitors; Antihypertensive agents; Cardiovascular Agents; Enzyme Inhibitors; Protease Inhibitors
Index of Refraction: 1.549 
Molar Refractivity: 99.53 cm3 
Molar Volume: 312.5 cm3  
Surface Tension: 51.2 dyne/cm 
Density: 1.204 g/cm3 
Flash Point: 306 °C 
Enthalpy of Vaporization: 91.58 kJ/mol 
Boiling Point: 582.4 °C at 760 mmHg 
Vapour Pressure of Enalapril (CAS NO.75847-73-3): 2.1E-14 mmHg at 25 °C

Enalapril Uses

  Enalapril (CAS NO.75847-73-3) is an angiotensin converting enzyme (ACE) inhibitor used in the treatment of hypertension and some types of chronic heart failure.

Enalapril Safety Profile

Safety Statements of Enalapril (CAS NO.75847-73-3): 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.

Enalapril Specification

  Enalapril (CAS NO.75847-73-3), its Synonyms are (S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline ; 1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester ; Bonuten ; Enalapril Richet ; Enalaprila ; L-Proline, 1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-, (S)- ; L-Proline, N-((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl- .

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