N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester
• CAS No.: 225517-65-7
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 225517-65-7.mol

Synonyms:N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester

Chemical Property of N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester

There total 13 articles about N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, 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:

(R)-3-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-propionic acid methyl ester (122871-98-1,832089-66-4) → N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester (225517-65-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 3.5h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)82374-6

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (R)-β-tyrosine methyl ester (177966-66-4) → N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester (225517-65-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0960-894X(02)00460-2

Reference yield:

p-benzyloxyaniline (6373-46-2) → N-tert-butoxycarbonyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid, methyl ester (225517-65-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. HBF₄ / ethanol

1.2: isoamyl nitrite / 5 °C

2.1: 10 percent Pd/C / methanol / 3 h / Heating

3.1: n-BuLi / 0.5 h / -78 °C

4.1: 93 percent / H₂ / 10 percent Pd/C / methanol / 2585.74 Torr

5.1: DIEA

With palladium on activated charcoal; tetrafluoroboric acid; n-butyllithium; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; 3.1: Michael addition;

DOI:10.1016/S0960-894X(02)00460-2

upstream raw materials:

(R)-3-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-propionic acid methyl ester

di-tert-butyl dicarbonate

(R)-β-tyrosine methyl ester

p-benzyloxyaniline

Downstream raw materials:

N-tert-butoxycarbonyl-3(R)-amino-3-(4-trifluoromethylsulfonyloxyphenyl)propionic acid, methyl ester