Methyl L-leucinate hydrochloride Chemical Properties

Melting point:

151-153 °C(lit.)

alpha 

20 º (c=4.5, MeOH)

refractive index 

13 ° (C=2, H2O)

storage temp. 

Inert atmosphere,2-8°C

solubility 

H₂O: 50 mg/mL, clear, colorless

form 

Crystals or Crystalline Powder

color 

White

optical activity

[α]22/D +13°, c = 2 in H2O

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

3595133

InChI

InChI=1/C7H15NO2.ClH/c1-5(2)4-6(8)7(9)10-3;/h5-6H,4,8H2,1-3H3;1H/t6-;/s3

InChIKey

DODCBMODXGJOKD-UZHXKHNSNA-N

SMILES

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

CAS DataBase Reference

7517-19-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37/39-27-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224995

MSDS

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

Methyl L-leucinate hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Leucine methyl ester is a protected form of L-Leucine (L330110). L-Leucine is an essential amino acid that induces a sharp decrease in blood glucose levels in individuals with idiopathic familial hypoglycemia, but has no known effects on normal, healthy individuals. L-Leucine also acts as an Isoleucine (I820210) antagonist in the rat, causing delays in growth, and is a potential tumour promoter of bladder cancer.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Under ice bath conditions, 60 mL of methanol was added to a 100 mL round bottom flask. 4 mL of sulfoxide chloride (SOCl2) was added slowly and dropwise through a constant pressure dropping funnel (with a drying tube fitted at the top), while the resulting off-gas was absorbed using NaOH solution. After stirring the reaction mixture for 1 h, 8 mmol of L-leucine was added and stirring was continued for 30 min at room temperature. Subsequently, the reaction system was warmed up to 66 °C and the reaction was refluxed for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) with an ethanol solution of 2% ninhydrin as the color developer until the raw material spot disappeared. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give L-leucine methyl ester hydrochloride in 100% yield.

References

[1] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0121
[2] Journal of Organic Chemistry, 2003, vol. 68, # 12, p. 5006 - 5008
[3] Synthetic Communications, 2010, vol. 40, # 8, p. 1161 - 1179
[4] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 63 - 77
[5] Chemical Biology and Drug Design, 2012, vol. 79, # 2, p. 216 - 222

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