Enalapril supplier | CasNO.75847-73-3

Name
Enalapril
EINECS
CAS No. 75847-73-3
Article Data16
CAS DataBase
Density 1.204 g/cm³
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
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms L-Proline,1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-, (S)-;
PSA 95.94000
LogP 1.93340

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 120924-94-9
N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

: 120379-81-9
5-phenylethyl-imidazolidine-2,4-dione

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9 2: 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 3: 95 percent / SOCl2 / 24 h / Ambient temperature 4: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 5: 85 percent / TFA / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 5 steps
1: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9
2: 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
3: 95 percent / SOCl2 / 24 h / Ambient temperature
4: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C
5: 85 percent / TFA / 3 h / Ambient temperature
View Scheme

: 121842-76-0
(R)-2-bromo-4-phenylbutyric acid

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / SOCl2 / 24 h / Ambient temperature 2: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 3: 85 percent / TFA / 3 h / Ambient temperature View Scheme

: 121842-77-1
(R)-ethyl 2-bromo-4-phenylbutyrate

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 2: 85 percent / TFA / 3 h / Ambient temperature View Scheme

: 121842-75-9
N-carbamyl (R)-2-amino-4-phenylbutyric acid

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 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 2: 95 percent / SOCl2 / 24 h / Ambient temperature 3: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 4: 85 percent / TFA / 3 h / Ambient temperature View Scheme

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 29 percent / H2, AcONa, AcOH, molecular sieves 3A / Raney Ni / ethanol 2: 93 percent / HCl / H2O / 4 h 3: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h 4: HCl / ethyl acetate View Scheme

: 2812-46-6
proline tert-butyl ester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h 2: HCl / ethyl acetate View Scheme

: 80828-38-2
N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / HCl / H2O / 4 h 2: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h 3: HCl / ethyl acetate View Scheme

: 80828-26-8
N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 1 h 2: HCl / ethyl acetate View Scheme
Multi-step reaction with 2 steps 1.1: (chloromethylene)dimethyliminium chloride / dichloromethane / 0.67 h / -10 - -5 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / methanol / 15 - 20 °C View Scheme

: 136622-17-8
N-<(2R)-2-(4-Toluenesulfonyloxy)propionyl>-L-proline Benzylester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / Et3N / dimethylsulfoxide / 8 h / 75 °C 2: hydrogen / 10percent Pd/C / ethanol / 2 h / 735.5 Torr / Ambient temperature View Scheme

: 84793-24-8
N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride

: 147-85-3
L-proline

A: 82717-96-2
[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

B: 76420-72-9
enalaprilate

C: 75847-73-3
enalapril

D: 115729-52-7
(S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester

Conditions

Conditions	Yield
Stage #1: N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride; L-proline In water; ethyl acetate at 19 - 20℃; for 5h; pH=10 - 11; Stage #2: at 30℃; for 0.166667h; pH=4.3 - 4.7;	A 0.5 %Chromat. B 0.4 %Chromat. C 14 %Chromat. D 0.5 %Chromat.
Stage #1: N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride; L-proline In dichloromethane; water at 19 - 20℃; for 5h; pH=9.5 - 11.5; Stage #2: at 30℃; for 0.166667h; pH=4.3 - 4.7;	A 0.5 %Chromat. B 0.5 %Chromat. C 10 %Chromat. D 0.6 %Chromat.
Stage #1: N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride; L-proline In water; ethyl acetate at 19 - 20℃; for 5h; pH=9.5 - 11.5; Stage #2: at 30℃; for 0.166667h; pH=4.3 - 4.7;	A 0.6 %Chromat. B 0.5 %Chromat. C 14 %Chromat. D 0.4 %Chromat.

...Expand

: 82717-96-2
[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

: 147-85-3
L-proline

: 75847-73-3
enalapril

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In DMF (N,N-dimethyl-formamide); acetonitrile at 20℃; for 0.5h;

aqueous pyridine: aqueous pyridine

L-alanyl-D-proline TFA salt: L-alanyl-D-proline TFA salt

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 75847-73-3
enalapril

Conditions

Conditions	Yield
With sodium cyanoborohydride; triethylamine In ethanol; water

...Expand

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 13485-59-1
L-alanyl-L-proline

A nitric salt: nitric salt

B: 75847-73-3
enalapril

Conditions

Conditions	Yield
aluminum nickel; silica gel In ethanol; acetic acid methyl ester; water; ethyl acetate

...Expand

: 16652-71-4
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

: 75847-73-3
enalapril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (chloromethylene)dimethyliminium chloride / dichloromethane / 0.67 h / -10 - -5 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / methanol / 15 - 20 °C View Scheme

: C20H26N2O6

: 75847-73-3
enalapril

Conditions

Conditions	Yield
With sulfuric acid; palladium on activated charcoal; hydrogen for 1h; Large scale;

: 75847-73-3
enalapril

: 149404-21-7
enalapril sodium salt

Conditions

Conditions	Yield
With sodium methylate In methanol	100%

: 75847-73-3
enalapril

: 110-16-7
maleic acid

: 76095-16-4
Amprace

Conditions

Conditions	Yield
at 5 - 30℃; for 7h;	92%
at 30 - 50℃; for 6h;	90%
In water at 5 - 60℃; for 4h;	90%

: 75847-73-3
enalapril

: 76420-72-9
enalaprilate

Conditions

Conditions	Yield
With sodium hydroxide for 24h; Ambient temperature;	75%
at 37℃; esterase from various rat tissue homogenates or plasma;
With recombinant human carboxylesterase 1; water In aq. phosphate buffer at 37℃; for 0.333333h; Kinetics; Enzymatic reaction;

: 75847-73-3
enalapril

: 115729-52-7
(S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester

Conditions

Conditions	Yield
In xylene for 5h; Heating;	60%

: 75847-73-3
enalapril

: (R)-2-((3S,8aR)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / xylene / 5 h / Heating 2: tetramethylammonium hydroxide / ethanol / 2 h View Scheme

: 75847-73-3
enalapril

: (S)-2-((3S,8aR)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / xylene / 5 h / Heating 2: tetramethylammonium hydroxide / ethanol / 2 h View Scheme

: 75847-73-3
enalapril

: enalaprilic acid

Conditions

Conditions	Yield
In sodium hydroxide
In sodium hydroxide

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- .

Product Name

Enalapril

Synthetic route

Enalapril Chemical Properties

Enalapril Uses

Enalapril Safety Profile

Enalapril Specification

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