D-Alanine Methyl Ester Hydrochloride Chemical Properties

Melting point:

108-110 °C(lit.)

alpha 

-8 º (c=1.6, MeOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Sparingly), Water (Slightly)

form 

Crystalline Powder

color 

White to off-white

optical activity

[α]20/D 8.0°, c = 1.6 in methanol

Water Solubility 

Soluble in Water 100 mg/ml.

InChI

InChI=1/C4H9NO2.ClH/c1-3(5)4(6)7-2;/h3H,5H2,1-2H3;1H/t3-;/s3

InChIKey

IYUKFAFDFHZKPI-DFWYDOINSA-N

SMILES

C(OC)(=O)[C@@H](C)N.[H]Cl |&1:4,r|

CAS DataBase Reference

14316-06-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

D-Alanine Methyl Ester Hydrochloride Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

D-Alanine methyl ester hydrochloride is used as building block for the preparation of peptides.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

GENERAL PROCEDURE: Thionyl chloride (SOCl?, 21.8 mL, 0.3 mol) and (S)-alanine (8.91 g, 0.1 mol) were added sequentially to methanol (CH?OH, 100 mL), and the reaction was stirred for 2 hours at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in methanol (30 mL) and again distilled under reduced pressure to remove the organic solvent. This dissolution-distillation process was repeated twice. The final colorless amorphous solid product, D-alanine methyl ester hydrochloride, was obtained with a melting point of 103 °C (literature value 98-99 °C) and a yield of 14.3 g (yield >99%).

References

[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 17, p. 4778 - 4799
[2] Organic Preparations and Procedures International, 2002, vol. 34, # 1, p. 87 - 94
[3] Tetrahedron Letters, 1989, vol. 30, # 3, p. 313 - 316
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6293 - 6305
[5] European Journal of Organic Chemistry, 2010, # 22, p. 4276 - 4287

D-Alanine Methyl Ester Hydrochloride(14316-06-4)Related Product Information

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