ChemicalBook CAS DataBase List N-METHYL-L-PHENYLALANINE HYDROCHLORIDE

N-METHYL-L-PHENYLALANINE HYDROCHLORIDE synthesis

3synthesis methods

Product Name:N-METHYL-L-PHENYLALANINE HYDROCHLORIDE
CAS Number:66866-67-9
Molecular formula:C10H13N1O2
Molecular Weight:215.68

67-56-1 Synthesis

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Yield:66866-67-9 100%

Reaction Conditions:

with thionyl chloride at 0 - 20; for 3 h;

Steps:

5.4 HCl·(N-Me)Phe-OMe (1a)

A solution of Boc-(N-Me)-Phe-OH (1 eq.) was dissolved in MeOH, then SOCl₂ (2.2 eq.) was added dropwise at 0°C. The reaction mixture was stirred at r.t. for 3h, then it was concentrated and treated several times with Et₂O. Finally it was evaporated under vacuum until to obtain the final product (quantitative). Rf=0.63 (CH₂Cl₂/MeOH 9:1). ¹HNMR (DMSO-d₆) δ: 2.95-3.02 (2H, m, β-CH₂), 3.30 (3H, s, N-CH₃), 3.75 (3H, s, COOCH₃), 4.82 (1H, m, α-CH), 7.05-7.41 (5H, m, Ar), 9.36 (3H, s, NH₃⁺). ESI-HRMS calcd for C₁₂H₁₇ClO₂m/z: 229.0995 [M+H]⁺; found 229.0992.

References:

Mollica, Adriano;Costante, Roberto;Stefanucci, Azzurra;Pinnen, Francesco;Luisi, Grazia;Pieretti, Stefano;Borsodi, Anna;Bojnik, Engin;Benyhe, Sándor [European Journal of Medicinal Chemistry,2013,vol. 68,p. 167 - 177]

L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, ethyl ester

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66866-67-9
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References

3081-24-1
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66866-67-9
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