Methyl L-histidinate dihydrochloride Chemical Properties

Melting point:

207 °C (dec.)(lit.)

alpha 

9 º (c=2 in H2O)

refractive index 

10 ° (C=2, H2O)

storage temp. 

Inert atmosphere,2-8°C

solubility 

100g/l

form 

Fine Crystalline Powder

color 

White

optical activity

[α]20/D +9.0°, c = 2 in H2O

Water Solubility 

Soluble in dimethyl sulfoxide, methanol and water.

Sensitive 

Hygroscopic

BRN 

3572010

InChI

InChI=1/C7H11N3O2.2ClH/c1-12-7(11)6(8)2-5-3-9-4-10-5;;/h3-4,6H,2,8H2,1H3,(H,9,10);2*1H/t6-;;/s3

InChIKey

DWAYENIPKPKKMV-ILKKLZGPSA-N

SMILES

C1(N=CNC=1)C[C@H](N)C(=O)OC.Cl.Cl |&1:6,r|

CAS DataBase Reference

7389-87-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29332900

MSDS

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

Methyl L-histidinate dihydrochloride Usage And Synthesis

Chemical Properties

Crystalline

Uses

L-Histidine methyl ester dihydrochloride is used to prepare optically pure L-(+)-ergothioneine.

Uses

Methyl L-histidinate dihydrochloride is used in the preparation of optically pure L-(+)-Ergothioneine.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Example 1; Synthesis of (R)-2-amino-3-(1H-imidazol-4-yl)propanoic acid methyl ester dihydrochloride was carried out by improving the method reported by Cook et al. In a 200 L Schott glass reactor equipped with an air-driven stirrer, a high-efficiency condenser and a gas introduction port, 12.5 kg of L-histidine hydrochloride monohydrate was suspended in 130 L of methanol. Dry HCl gas was passed into the suspension while the mixture was heated to 55-65 °C until complete dissolution. The passage of HCl gas was continued until saturation, at which point it was stopped. Shortly after the solution was formed, a precipitation of the product began to appear. The mixture is stirred continuously and supplemented with additional passes of HCl gas every 1 hour and 15 minutes; the mixture is heated under mild reflux conditions for 8 hours. After the reaction is complete, it can be kept warm for 6-8 hours. Subsequently, 40 L of ethyl acetate is added, stirred for 1 hour and filtered. The filter cake was washed with 10 L of isopropyl ether and the resulting white crystalline product was air dried. The yield was 95%. The melting point was 102-103 °C (literature value 102-103 °C). Spinodal [α]25D = +3.5° (c=2, H2O).1H NMR (D2O) data: δ 3.4 (t, 2H), 3.9 (s, 3H), 4.5 (s, 2H), 7.4 (s, 1H), 8.5 (s, 1H).

References

[1] Tetrahedron Asymmetry, 2008, vol. 19, # 3, p. 273 - 278
[2] Patent: US2009/93642, 2009, A1. Location in patent: Page/Page column 6; 7

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