Product Name

  • Name

    ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate

  • EINECS
  • CAS No. 37178-37-3
  • Article Data6
  • CAS DataBase
  • Density 1.279 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H15NO4
  • Boiling Point 394.246 °C at 760 mmHg
  • Molecular Weight 225.244
  • Flash Point 192.233 °C
  • Transport Information
  • Appearance
  • Safety 26
  • Risk Codes 22-36
  • Molecular Structure Molecular Structure of 37178-37-3 (ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate)
  • 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;
  • PSA 92.78000
  • LogP 1.23100

Synthetic route

ethanol
64-17-5

ethanol

levodopa
59-92-7

levodopa

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

Conditions
ConditionsYield
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;
levodopa
59-92-7

levodopa

ascorbic acid
50-81-7

ascorbic acid

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

Conditions
ConditionsYield
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water88%
With thionyl chloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; sodium sulfate In ethanol; water88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

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

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

Conditions
ConditionsYield
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
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

levodopa
59-92-7

levodopa

Conditions
ConditionsYield
With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent;
3-Bromoindan-1-one
40774-41-2

3-Bromoindan-1-one

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

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

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

Conditions
ConditionsYield
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
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

carbidopa monohydrate

carbidopa monohydrate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

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

ethyl 3-(3,4-(dibenzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C
2: potassium carbonate / acetone / 48 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

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

ethyl 2-amino-3-(3,4-(dibenzyloxy)phenyl)propanoate

Conditions
ConditionsYield
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
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

C23H22N2O3

C23H22N2O3

Conditions
ConditionsYield
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
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

C23H24N2O2

C23H24N2O2

Conditions
ConditionsYield
Multi-step reaction with 7 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
7.1: dimethyl sulfide borane / tetrahydrofuran / 30 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

ethyl 3-(3,4-bis(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate

ethyl 3-(3,4-bis(benzyloxy)phenyl)-2-(1,3-dioxoisoindolin-2-yl)propanoate

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: toluene / 24 h / Reflux
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

(S)-2-(6,7-bis(benzyloxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)isoindoline-1,3-dione

(S)-2-(6,7-bis(benzyloxy)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 5 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
View Scheme
L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

tert-butyl ((S)-3-(benzyloxy)-1-(((S)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroquinolin-3-yl)amino)-1-oxopropan-2-yl)carbamate

tert-butyl ((S)-3-(benzyloxy)-1-(((S)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroquinolin-3-yl)amino)-1-oxopropan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 8 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
7.1: dimethyl sulfide borane / tetrahydrofuran / 30 h / Reflux
8.1: benzyl chloroformate; 4-methyl-morpholine / dichloromethane / 6 h / -78 - 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-DOPA ethyl ester
37178-37-3

L-DOPA ethyl ester

N-(tert-butoxycarbonyl)-3,4-(dihydroxy)-L-phenylalanine ethyl ester
1313214-06-0

N-(tert-butoxycarbonyl)-3,4-(dihydroxy)-L-phenylalanine ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 16h;

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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