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Cas Database

Name	Etilevodopa	EINECS	N/A
CAS No.	37178-37-3	Density	1.279 g/cm³
PSA	92.78000	LogP	1.23100
Solubility	N/A	Melting Point	N/A
Formula	C₁₁H₁₅NO₄	Boiling Point	394.246 °C at 760 mmHg
Molecular Weight	225.244	Flash Point	192.233 °C
Transport Information	N/A	Appearance	N/A
Safety	26	Risk Codes	22-36
Molecular Structure		Hazard Symbols	Xn
Synonyms	3,4-Dihydroxy-L-phenylalanineethyl ester;3-Hydroxy-L-tyrosine ethyl ester;L-Dopa ethyl ester;Levodopa ethyl ester;O-Ethyl-DOPA;Ethyl 3-hydroxy-L-tyrosinate;	Article Data	6

Etilevodopa Synthetic route

: 64-17-5
ethanol

: 59-92-7
levodopa

: 37178-37-3
L-DOPA ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride Fischer esterification;	100%
With hydrogenchloride Fisher esterfication;	100%
With thionyl chloride 1.) 0 deg C, 2 h, 2.) room temperature, overnight;
With thionyl chloride for 24h; Reflux;

: 59-92-7
levodopa

: 50-81-7
ascorbic acid

: 37178-37-3
L-DOPA ethyl ester

Conditions

Conditions	Yield
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water	88%
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water	88%

: 24424-99-5
di-tert-butyl dicarbonate

: 37178-37-3
L-DOPA ethyl ester

: 203398-44-1
N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%
With triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	97%
With triethylamine In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) room temperature, 48 h;	42.1 g

: 37178-37-3
L-DOPA ethyl ester

: 59-92-7
levodopa

Conditions

Conditions	Yield
With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent;

: 40774-41-2
3-Bromoindan-1-one

: 37178-37-3
L-DOPA ethyl ester

: 3-(3,4-dihydroxyphenyl)-2-(3-oxoindan-1-ylamino)propionic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃;

: 37178-37-3
L-DOPA ethyl ester

: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 42.1 g / triethylamine / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 48 h 2: 43 percent Turnov. / CF3CO2Ag, I2 / CH2Cl2 / 24 h / Ambient temperature View Scheme

: 37178-37-3
L-DOPA ethyl ester

: carbidopa monohydrate

: 37178-37-3
L-DOPA ethyl ester

: 69344-36-1
ethyl 3-(3,4-(dibenzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C 2: potassium carbonate / acetone / 48 h / Reflux View Scheme

: 37178-37-3
L-DOPA ethyl ester

: 69295-27-8
ethyl 2-amino-3-(3,4-(dibenzyloxy)phenyl)propanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C 2: potassium carbonate / acetone / 48 h / Reflux 3: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C View Scheme

: 37178-37-3
L-DOPA ethyl ester

: C23H22N2O3

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C 2.1: potassium carbonate / acetone / 48 h / Reflux 3.1: trifluoroacetic acid / dichloromethane / 26 h / 0 - 20 °C 4.1: toluene / 24 h / Reflux 5.1: acetic acid; nitric acid / 1.5 h / 0 °C 5.2: 1.5 h / 80 °C 6.1: hydrazine hydrate / ethanol / 40 h / Reflux View Scheme

Etilevodopa Specification

The Etilevodopa, with the CAS registry number 37178-37-3, is also known as 3-Hydroxy-L-tyrosine ethyl ester. This chemical's molecular formula is C₁₁H₁₅NO₄ and molecular weight is 225.24. What's more, its systematic name is Ethyl 3-hydroxy-L-tyrosinate. Its classification code is Antiparkisonian. This chemical is a dopaminergic agent which is used as a treatment for Parkinson's disease. It is the ethyl ester of levodopa.

Physical properties of Etilevodopa are: (1)ACD/LogP: 0.347; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.40; (4)ACD/LogD (pH 7.4): 0.10; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 21.04; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 92.78 Å²; (13)Index of Refraction: 1.581; (14)Molar Refractivity: 58.733 cm³; (15)Molar Volume: 176.167 cm³; (16)Polarizability: 23.283×10^-24cm³; (17)Surface Tension: 57.2 dyne/cm; (18)Density: 1.279 g/cm³; (19)Flash Point: 192.233 °C; (20)Enthalpy of Vaporization: 66.939 kJ/mol; (21)Boiling Point: 394.246 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)[C@@H](N)Cc1cc(O)c(O)cc
(2)Std. InChI: InChI=1S/C11H15NO4/c1-2-16-11(15)8(12)5-7-3-4-9(13)10(14)6-7/h3-4,6,8,13-14H,2,5,12H2,1H3/t8-/m0/s1
(3)Std. InChIKey: NULMGOSOSZBEQL-QMMMGPOBSA-N

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