2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide

Base Information

• Chemical Name: 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide
• CAS No.: 722499-78-7
• Molecular Formula: C₂₂H₂₈N₂O₄
• Molecular Weight: 384.475
• Mol file: 722499-78-7.mol

Synonyms:2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide

Chemical Property of 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide

There total 1 articles about 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide 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: 95.0%

tyrosamine (51-67-2) + Boc-D-Phe-OH (18942-49-9) → 2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide (722499-78-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/anie.200353636 DOI:10.1248/cpb.54.1662

Reference yield: 97.0%

2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide (722499-78-7) → 2-(R)-amino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide (722499-70-9)

Guidance literature:

With methanesulfonic acid; In methanol; at 40 ℃; for 3h;

DOI:10.1002/anie.200353636 DOI:10.1248/cpb.54.1662

Reference yield:

2-(R)-tert-butoxycarbonylamino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide (722499-78-7) → C27H25F3N2O5 (722499-81-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 97 percent / methanesulfonic acid / methanol / 3 h / 40 °C

2.1: dioxane / 24 h / 20 °C

2.2: 64 percent / HCl / dioxane / 24 h / 20 °C

3.1: 94 percent / pyridine / 0.25 h / 0 °C

4.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C

5.1: 95 percent / BCl₃ / CH₂Cl₂ / 20 h / -78 °C

6.1: 83 percent / pyridine / 3 h / 0 °C

7.1: 98 percent / formic acid; Et₃N; PPh₃ / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C

8.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C

With pyridine; formic acid; methanesulfonic acid; boron trichloride; L-Selectride; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; 5.1: Michael addition;

DOI:10.1248/cpb.54.1662

upstream raw materials:

tyrosamine

Boc-D-Phe-OH

Downstream raw materials:

2-(R)-amino-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropionamide

C₂₅H₂₆N₂O₅

C₂₇H₂₅F₃N₂O₅

C₂₇H₂₃F₃N₂O₅