L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-, methyl ester

Base Information

• Chemical Name: L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-, methyl ester
• CAS No.: 138908-56-2
• Molecular Formula: C17H25NO6
• Molecular Weight: 339.389
• Mol file: 138908-56-2.mol

Synonyms:(L)-N-tert-butoxycarbonyl-3,4-dimethoxyphenylalanine methyl ester;methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dimethoxyphenyl)propanoate;(S)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester;

Chemical Property of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-, methyl ester

Chemical Property:

• Melting Point: 77-78 °C(Solv: heptane (142-82-5); ethyl acetate (141-78-6))
• Boiling Point: 463.8±45.0 °C(Predicted)
• PSA: 83.09000
• Density: 1.123±0.06 g/cm3(Predicted)
• LogP: 2.70350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1,1-Dimethylethoxy)carbonyl]-3-methoxy-O-methyl-L-tyrosine Methyl Ester is an intermediate used in the synthesis of N-Methyl-L-DOPA (M303825), which is a methylated L-DOPA that can act as a potential alternative substrate or competitive inhibitor of tyrosinase.

Technology Process of L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-, methyl ester

There total 9 articles about L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-, methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate (37169-36-1) + methyl iodide (74-88-4) → (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (138908-56-2)

Guidance literature:

With potassium carbonate; In acetone; for 6h; Reflux;

DOI:10.1021/tx9003374

Reference yield: 98.0%

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate (37169-36-1) + dimethyl sulfate (77-78-1) → (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (138908-56-2)

Guidance literature:

With potassium carbonate; In acetone; for 41.5h; Reflux;

DOI:10.1002/cmdc.202000153

Reference yield: 94.4%

di-tert-butyl dicarbonate (24424-99-5) + L-DOPA methyl ester (7101-51-1) → (S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (138908-56-2)

Guidance literature:

L-DOPA methyl ester; With thionyl chloride; In methanol; at 50 ℃; for 3h; Inert atmosphere; Cooling with ice;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 1h; Cooling with ice;

With potassium carbonate; dimethyl sulfate; In acetone; at 20 ℃; Reflux;

upstream raw materials:

(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoic acid

methyl iodide

dimethyl sulfate

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid

Downstream raw materials:

trans-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester

(S)-4-(3,4-dimethoxybenzyl)oxazolidin-2-one

(4S)-4-(3,4-dimethoxybenzyl)-3-(propa-1,2-dienyl)oxazolidin-2-one

C₁₅H₁₇NO₄