L-Methionine methyl ester hydrochloride Chemical Properties

Melting point:

151-153 °C(lit.)

alpha 

26 º (c=5, H2O 24 ºC)

refractive index 

26 ° (C=1, H2O)

storage temp. 

Inert atmosphere,2-8°C

solubility 

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

form 

Powder

color 

White to beige

optical activity

[α]22/D +25.9°, c = 1 in H2O

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

BRN 

3913214

InChI

InChI=1/C6H13NO2S.ClH/c1-9-6(8)5(7)3-4-10-2;/h5H,3-4,7H2,1-2H3;1H/t5-;/s3

InChIKey

MEVUPUNLVKELNV-USHJBNIQNA-N

SMILES

[C@H](N)(CCSC)C(=O)OC.Cl |&1:0,r|

CAS DataBase Reference

2491-18-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-26

WGK Germany 

3

HS Code 

29309090

MSDS

• Language:English Provider:Methyl L-methionate hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L-Methionine methyl ester hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Methionine methyl ester hydrochloride is used as a starting material for the synthesis of a protected glycine derivative, a versatile asymmetric building block.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Synthesis Example 1: L-methionine (0.5 g, 1 eq.) was suspended in a 100 mL round-bottomed flask fitted with a magnetic stirrer, methanol (30 mL, concentration 0.1 M) was added and cooled to 0°C under nitrogen atmosphere. Thionyl chloride (0.5 mL, 2 equiv.) was added slowly and dropwise to the above suspension, followed by heating and refluxing the reaction for 16 hours. After completion of the reaction, the solvent was removed by rotary evaporator to give a light yellow solid. The solid was ground with hot ether and the ether solution was removed by filtration to give a white solid L-methionine methyl ester hydrochloride (0.65561 g, 98% yield). The product was further purified by vacuum drying.1H NMR (D2O, 500 MHz) δH: 4.24 (1H, m, CH), 3.79 (3H, s, OCH3), 2.63 (2H, t, CH2), 2.25 (1H, m, CH2), 2.16 (1H, m, CH2), 2.06 (1H, s, SCH3). 13C NMR (D2O, 125 MHz) δC: 170.58 (C=O), 53.64 (OCH3), 51.70 (CH), 28.71 (CH2), 28.41 (CH2), 13.85 (SCH3). IR (neat, vmax, cm-1): 2880.8/2676.2 (CH3, CH2, CH), 2016.2, 1742.2 (C=O, ester), 1483.6, 1443.5, 1227, 1194.7, 1149.8, 1079.5 (C-O). HRMS m/z (+ESI): C6H14NO2S, calculated mass = 164.074 (error = 0.07 ppm).

References

[1] Journal of Organic Chemistry, 2011, vol. 76, # 1, p. 201 - 215
[2] Journal of the American Chemical Society, 2017, vol. 139, # 40, p. 14077 - 14089
[3] Patent: WO2012/131313, 2012, A1. Location in patent: Page/Page column 49
[4] Patent: US2014/39200, 2014, A1. Location in patent: Paragraph 0376-0380
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944

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