Methyl L-isoleucinate hydrochloride Chemical Properties

Melting point:

98-100 °C

alpha 

27 º (c=2% in H2O)

refractive index 

26.5 ° (C=2, H2O)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in methanol (50 mg/ml clear, colorless solution).

form 

Powder or Crystalline Powder

color 

Off-white to orange

optical activity

[α]20/D +27.0±1°, c = 2% in H2O

Sensitive 

Hygroscopic

BRN 

3595132

Stability:

Hygroscopic

InChI

InChI=1/C7H15NO2.ClH/c1-4-5(2)6(8)7(9)10-3;/h5-6H,4,8H2,1-3H3;1H/t5-,6-;/s3

InChIKey

GGTBEWGOPAFTTH-ATPDZTHWNA-N

SMILES

[C@@H](N)(C(=O)OC)[C@@H](C)CC.Cl |&1:0,6,r|

CAS DataBase Reference

18598-74-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-40

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl L-isoleucinate hydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Isoleucine methyl ester used for chemical synthesis. E.g. It can also be used to produce 3-methyl-2-(4-nitro-imidazol-1-yl)-pentanoic acid methyl ester. It also finds its use as a pharmaceutical intermediate.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Under ice bath conditions, 1 mL of sulfuryl chloride (SOCl2) was added slowly and dropwise to 5 mL of cooled methanol and the reaction mixture was stirred for 30 minutes. Subsequently, 1.01 g (8.55 mmol) of L-isoleucine was added to the mixture and the reaction was continued with stirring overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by fast column chromatography with an eluent ratio of methanol/ether = 1/5 (v/v), resulting in the colorless oily crystalline product L-isoleucine methyl ester hydrochloride in 98.8% yield. The spectral data of the product were consistent with those reported in the literature.

References

[1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 44, p. 9372 - 9378
[2] Angewandte Chemie, 1992, vol. 104, # 1, p. 97 - 99
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 8, p. 2747 - 2761
[4] Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 63 - 77
[5] Angewandte Chemie - International Edition, 2018, vol. 57, # 36, p. 11683 - 11687

Methyl L-isoleucinate hydrochloride(18598-74-8)Related Product Information

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• L-Isoleucine benzyl ester 4-toluenesulphonate
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• L-Isoleucine tert-butyl ester hydrochloride