benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate

Base Information

• Chemical Name: benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate
• CAS No.: 468721-44-0
• Molecular Formula: C₃₂H₃₄N₂O₆
• Molecular Weight: 542.632
• Mol file: 468721-44-0.mol

Synonyms:benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate

Chemical Property of benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate

There total 11 articles about benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate 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: 81.0%

benzyl alcohol (100-51-6,185532-71-2) + (S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one (468721-43-9) → benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate (468721-44-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T

Reference yield: 31.0%

C32H37N3O7 + benzyl alcohol (100-51-6,185532-71-2) → benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate (468721-44-0)

Guidance literature:

benzyl alcohol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

C₃₂H₃₇N₃O₇; In tetrahydrofuran; hexane; at -78 - 0 ℃;

DOI:10.1016/j.tetasy.2008.12.023

Reference yield:

Methyl indole-3-propionate (5548-09-4) → benzyl (2R)-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propanoate (468721-44-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / DMAP / acetonitrile / 2.5 h / 20 °C

2.1: 94 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 9 h / 20 °C

3.1: pivaloyl chloride; Et₃N / tetrahydrofuran / 1.5 h / -30 °C

3.2: 83 percent / LiCl / tetrahydrofuran / 11 h / -30 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C

4.2: 76 percent / tetrahydrofuran / 3 h / -78 °C

5.1: 100 percent / H₂ / Pd/C / tetrahydrofuran / 4 h

6.1: 74 percent / diphenylphosphoryl azide; Et₃N / toluene / 1 h / Heating

7.1: 81 percent / nBuLi / tetrahydrofuran; hexane / 3 h / 0 °C

With dmap; lithium hydroxide; n-butyllithium; diphenylphosphoranyl azide; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; water; toluene; acetonitrile;

DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T

upstream raw materials:

benzyl alcohol

(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

Methyl indole-3-propionate

di-tert-butyl dicarbonate

Refernces

• 1、 Micuch, Peter,Seebach, Dieter. "Preparation of β2-homotryptophan derivatives for β-peptide synthesis". . p. 1567 - 1577. Retrieved 2007/10/03.