N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine supplier

Name
N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine
EINECS 1308068-626-2
CAS No. 82717-96-2
Article Data20
CAS DataBase
Density 1.137 g/cm³
Solubility 100mg/L at 25℃
Melting Point 150-152 °C(lit.)
Formula C₁₅H₂₁NO₄
Boiling Point 441.2 °C at 760 mmHg
Molecular Weight 279.336
Flash Point 220.6 °C
Transport Information
Appearance White crystalline powder
Safety 37/39-26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzenebutanoicacid, a-[(1-carboxyethyl)amino]-,monoethyl ester, [S-(R*,R*)]-;Benzenebutanoic acid, a-[[(1S)-1-carboxyethyl]amino]-,monoethyl ester, (aS)- (9CI);N-[(S)-1-Ethoxycarbonyl-3-phenylpropyl]-L-alanine;N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine;N-(1-(S)-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanine(ECPPA);
PSA 75.63000
LogP 2.00450

Synthetic route

: 87269-98-5
(1'S,2S)-2-(1'-Methyl-2'-oxo-2'-phenylmethoxy-ethylamino)-4-oxo-4-phenyl-buttersaeure-ethylester

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

Conditions

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen; N,N-diphenylthiourea In 1,4-dioxane; isopropyl alcohol under 2250.23 Torr; Reagent/catalyst; Solvent; Autoclave;	96%
With sulfuric acid; hydrogen; palladium on activated charcoal In acetic acid at 25 - 30℃; under 760 Torr;	91%
With methanesulfonic acid; hydrogen; palladium on activated charcoal In isopropyl alcohol at 20 - 215℃; for 10h;

: 97457-39-1
Benzyl (2S)-2-amino>propionate Hydrogenmaleate

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

Conditions

Conditions	Yield
With hydrogen; palladium In ethanol under 760 Torr; for 3h; Ambient temperature;	96%

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

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

Conditions

Conditions	Yield
With trifluoroacetic acid for 2h; Ambient temperature;	90%
With trifluoroacetic acid

: 82717-95-1
Benzyl (2S)-2-amino>propionate

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

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; Ambient temperature;
Multi-step reaction with 2 steps 1: ethyl acetate; diisopropyl ether 2: 96 percent / H2 / Pd / ethanol / 3 h / 760 Torr / Ambient temperature View Scheme

: 46460-23-5
ethyl 2-amino-4-phenyl-(2S)-butyrate

: 93836-48-7
(S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester

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

B: 85196-26-5
(2R)-2-amino>propionic acid

Conditions

Conditions	Yield
With formic acid; tributyl-amine; palladium on activated charcoal 1.) CH2Cl2, -20 deg C, 2 h, 2.) methanol, 2 h; Yield given. Multistep reaction;

...Expand

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O; nitromethane / 72 h / 50 °C / examined various solvent-base systems 2: 90 percent / CF3COOH / 2 h / Ambient temperature View Scheme

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

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

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: H2O; nitromethane / 72 h / 50 °C / examined various solvent-base systems 4: 90 percent / CF3COOH / 2 h / Ambient temperature View Scheme

: 15121-89-8
ethyl (E)-4-oxo-4-phenyl-2-butenoate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / N(C2H5)3 / ethanol / Ambient temperature 2: 91 percent / H2, cc.H2SO4 / Pd/C / acetic acid / 25 - 30 °C / 760 Torr View Scheme

: 93921-85-8
ethyl 2-hydroxy-4-phenylbutanoate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / pyridine / CH2Cl2 / 0 °C 2: N(C2H5)3 / CH2Cl2 / Ambient temperature 3: H2 / Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

: 29678-81-7
(R)-2-hydroxy4-phenylbutanoic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: HCl 2: pyridine / CH2Cl2 / Ambient temperature 3: N(C2H5)3 / CH2Cl2 / Ambient temperature 4: H2 / Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

: 90315-82-5
ethyl (R)-2-hydroxy-4-phenylbutyrate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / Ambient temperature 2: N(C2H5)3 / CH2Cl2 / Ambient temperature 3: H2 / Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

: 90365-91-6, 150822-65-4
(-)-α-[(Trifluoromethyl)sulfonyl]oxy-4-phenylbutyric acid,ethyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N(C2H5)3 / CH2Cl2 / Ambient temperature 2: H2 / Pd/C / ethanol / 760 Torr / Ambient temperature View Scheme

: 88767-98-0
ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N(C2H5)3 / CH2Cl2 / Ambient temperature 2: H2 / Pd/C / ethanol / 760 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

: ethyl (R)-2-fluorosulfonyloxy-4-phenylbutanoate

: 17831-01-5
H-Ala-OBzl

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

Conditions

Conditions	Yield
Stage #1: ethyl (R)-2-fluorosulfonyloxy-4-phenylbutanoate; H-Ala-OBzl With triethylamine In acetonitrile at 20 - 40℃; for 2.5h; Stage #2: With hydrogen; palladium In ethanol under 1810.07 Torr; for 0.2h;

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

: 42854-62-6
L-alanine benzyl ester p-toluenesulfonate

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

Conditions

Conditions	Yield
With 4-methyl-morpholine In methanol; cyclohexane

: 79-37-8
oxalyl dichloride

: 93921-85-8
ethyl 2-hydroxy-4-phenylbutanoate

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

: 13404-22-3
tert-butyl L-alaninate hydrochloride

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

Conditions

Conditions	Yield
With sodium ethanolate; sodium cyanoborohydride; sodium hydrogencarbonate In ethanol

...Expand

: benzyl (R)-α-toluenesulfonyloxypropionate

: 46460-23-5
ethyl 2-amino-4-phenyl-(2S)-butyrate

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

Conditions

Conditions	Yield
In water; potassium carbonate; acetonitrile

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

: 541-41-3
chloroformic acid ethyl ester

: ethyl 2-(S)-{N-ethoxycarbonyl-N-[1-(S)-(ethoxycarbonyloxycarbonyl)-ethyI]-amino}-4-phenylbutyrate

Conditions

Conditions	Yield
With triethylamine In acetone at -2 - 20℃; for 1.5h;	100%

: (2S,3aS,6aS)-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester hydrochloride

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

: 87269-88-3
2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester

Conditions

Conditions	Yield
Stage #1: [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine With hydrogenchloride; thionyl chloride; N,N-dimethyl-formamide In dichloromethane at -10 - -5℃; for 0.00416667h; Inert atmosphere; Stage #2: (2S,3aS,6aS)-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester hydrochloride With sodium hydrogencarbonate In dichloromethane; water for 0.005h;	99.5%

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

: 83402-63-5
tert-butyl N-(2,3-dihydro-1H-inden-2-yl)glycinate

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 83435-61-4
N-(2,3-dihydro-1H-inden-2-yl)-N--L-alanyl>-glycine t-butyl ester

Conditions

Conditions	Yield
With sodium hydroxide; phosphoric acid; triethylamine In dichloromethane; water	98%

...Expand

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

: (S)-N-[(S)-1-CARBAMOYL-3-PHENYLPROPYL]-ALANINE

Conditions

Conditions	Yield
	96%

: tert-butyl (2S,3aR,7aS)-octahydro-1H-indole-2-carboxylate

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

: tert-butyl (2S,3aR,7aS)-1-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydro-1H-indole-2-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 17h; Inert atmosphere;	95%

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

: 114192-42-6
N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; phosphorus pentachloride In 1,4-dioxane; dichloromethane at 0 - 20℃; for 16.5h;	93%
With phosphorus pentachloride In dichloromethane at 0℃;
With phosphorus pentachloride In dichloromethane at 0℃;

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

: 80875-98-5
(2S,3aS,7aS)-perhydroindole-2-carboxylic acid

: ramipril

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;	92%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

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

: 89371-34-6
N-succinimidyl (2S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propionate

Conditions

Conditions	Yield
With sodium hydrogencarbonate; chlorophosphoric acid diphenyl ester In acetone at 50℃; for 1h;	86%
With dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 18h; Ambient temperature;

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

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: N-[(1S)-1-Ethoxycarbonyl-3-Phenylpropyl]-N-(2,2,2-Trichloroethoxycarbonyl)-1-Alanine

Conditions

Conditions	Yield
With pyridine; hydrogenchloride In dichloromethane; cyclohexane; water	70%
With triethylamine In dichloromethane

N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine Specification

The IUPAC name of N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine is (2S)-2-[[(2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azaniumyl]propanoate. With the CAS registry number 82717-96-2, it is also named as Benzenebutanoic acid, alpha-((1-carboxyethyl)amino)-, monoethyl ester, (S-(theta,theta))-. The product's categories are miscellaneous; various intermediates; amino acids 13C, 2H, 15N; amino acids & derivatives; aromatics; chiral reagents; intermediates; intermediates & fine chemicals; metabolites & impurities; pharmaceuticals; alanine derivatives; peptide synthesis; unnatural amino acid derivatives. It is white crystalline powder which is an intermediate in the synthesis of Ramipril. It is also used as Moexipril intermediate. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine can be summarized as: (1)ACD/LogP: 2.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.5; (4)ACD/LogD (pH 7.4): -0.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.28; (8)ACD/KOC (pH 7.4): 1.13; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.523; (13)Molar Refractivity: 75.08 cm³; (14)Molar Volume: 245.4 cm³; (15)Polarizability: 29.76×10^-24 cm³; (16)Surface Tension: 43.8 dyne/cm; (17)Enthalpy of Vaporization: 73.61 kJ/mol; (18)Vapour Pressure: 1.46E-08 mmHg at 25°C; (19)Rotatable Bond Count: 8; (20)Exact Mass: 279.147058; (21)MonoIsotopic Mass: 279.147058; (22)Topological Polar Surface Area: 83; (23)Heavy Atom Count: 20; (24)Complexity: 308.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@@H](N[C@H](C(=O)OCC)CCc1ccccc1)C
2. InChI:InChI=1/C15H21NO4/c1-3-20-15(19)13(16-11(2)14(17)18)10-9-12-7-5-4-6-8-12/h4-8,11,13,16H,3,9-10H2,1-2H3,(H,17,18)/t11-,13-/m0/s1

Product Name

N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine

Synthetic route

N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine Specification

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