Methyl L-tyrosinate hydrochloride Chemical Properties

Melting point:

192 °C (dec.)(lit.)

alpha 

74 º (c=3,1N pyridine)

refractive index 

13 ° (C=2, MeOH)

storage temp. 

2-8°C

Water Solubility 

very faint turbidity in Water

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

powder to crystal

color 

White to Almost white

optical activity

[α]25/D +74.0°, c = 3 in pyridine

Sensitive 

Hygroscopic

BRN 

3917353

InChI

InChI=1/C10H13NO3.ClH/c1-14-10(13)9(11)6-7-2-4-8(12)5-3-7;/h2-5,9,12H,6,11H2,1H3;1H/t9-;/s3

InChIKey

VXYFARNRGZWHTJ-OVMXBOEKNA-N

SMILES

C1(C=CC(O)=CC=1)C[C@H](N)C(=O)OC.Cl |&1:8,r|

CAS DataBase Reference

3417-91-2(CAS DataBase Reference)

EPA Substance Registry System

L-Tyrosine, methyl ester, hydrochloride (3417-91-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29225000

MSDS

• Language:English Provider:L-Tyrosine methyl ester hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl L-tyrosinate hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

1. Acetyl chloride (21.32 mL, 300 mmol) was slowly added dropwise to 200 mL of anhydrous methanol under ice bath conditions with stirring for 30 minutes. 2. L-tyrosine (18.1 g, 100 mmol) was added to the above solution, followed by transferring the reaction mixture to an oil bath and heating to reflux for 4 hours. 3. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Appropriate amount of acetone was added to the residue and filtered to obtain white powdery L-tyrosine methyl ester hydrochloride (22.78 g, 99% yield). 4. Di-tert-butyl dicarbonate (11.34 g, 52 mmol) was dissolved in 50 mL of 1,4-dioxane and slowly added to 160 mL of mixed solvent (1,4-dioxane-H2O = 1:1) containing L-tyrosine methyl ester hydrochloride (9.26 g, 40 mmol) and K2CO3 (8.28 g, 60 mmol). 5. After stirring the reaction mixture at room temperature overnight, the solvent was removed by concentration under reduced pressure. EtOAc was added for extraction and the EtOAc layer was washed sequentially with 1N citric acid, saturated NaHCO3 solution and brine. 6. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give compound 2 in white powder form, which can be used in subsequent steps without further purification.

References

[1] Synthetic Communications, 1992, vol. 22, # 7, p. 979 - 985
[2] Tetrahedron, 2001, vol. 57, # 39, p. 8313 - 8322
[3] Chemistry - A European Journal, 2011, vol. 17, # 22, p. 6206 - 6213
[4] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660
[5] Heterocycles, 2002, vol. 56, # 1-2, p. 157 - 170

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