ChemicalBook CAS DataBase List N-ME-PHE-OME HCL

N-ME-PHE-OME HCL synthesis

4synthesis methods

Product Name:N-ME-PHE-OME HCL
CAS Number:19460-86-7
Molecular formula:C11H16ClNO2
Molecular Weight:229.7

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

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Yield:19460-86-7 91.2%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;dichloromethane at 0 - 20; for 1 h;

Steps:

4.3.1. Cleavage of N^α-Boc group with hydrogen chloride in dioxane

General procedure: A solution of HCl (3.3 M) in dioxane (5 mL) was added to a stirred solution of N^α-Boc-protected peptide (1 mmol) in DCM (2 mL) at 0 °C. The temperature was risen to 20 °C and the solution maintained for 1 h. The solvents were removed under vacuum and the residue stirred in dry ether to produce a crystalline product. In case of the poorly crystallizing or highly hygroscopic compounds the residual material was dissolved in dry chloroform, the solution evaporated and the product dried in a vacuum desiccator over P₄O₁₀ or KOH. Some products were purified by chromatography using silica gel and eluent mixture B, or by gel filtration on biogel P2 or fractogel TCK HW 40 with subsequent lyophilization.

References:

Ryakhovsky, Vladimir V.;Ivanov, Andrey S. [Tetrahedron,2012,vol. 68,# 35,p. 7070 - 7076] Location in patent:supporting information; experimental part

7524-50-7 Synthesis