N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine
• CAS No.: 1261352-25-3
• Molecular Formula: C₂₀H₂₆N₄O₆
• Molecular Weight: 418.45
• Mol file: 1261352-25-3.mol

Synonyms:N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine

Chemical Property of N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine

There total 5 articles about N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine 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: 64.0%

(S)-2-azido-3-phenylpropionic acid methyl ester (116911-32-1) + (S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid (61172-66-5,63039-46-3,63039-48-5,143979-37-7) → N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine (1261352-25-3)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.bmcl.2010.09.139

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine (1261352-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(ll) sulfate pentahydrate; triflic azide; triethylamine / water; acetonitrile / 0.5 h / 0 °C

2: thionyl chloride / 0 - 20 °C / Inert atmosphere

3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

With thionyl chloride; copper(ll) sulfate pentahydrate; triflic azide; sodium L-ascorbate; triethylamine; In water; acetonitrile; tert-butyl alcohol; 3: Huisgen Cycloaddition;

DOI:10.1016/j.bmcl.2010.09.139

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-4-yl}-L-alanine (1261352-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane; water / 2.25 h / 0 - 20 °C

2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 20 °C

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; sodium hydroxide; In 1,4-dioxane; water; tert-butyl alcohol; 2: Huisgen Cycloaddition;

DOI:10.1016/j.bmcl.2010.09.139

upstream raw materials:

L-phenylalanine

di-tert-butyl dicarbonate

(2S)-2-amino-4-pentynoic acid

(2S)-2-azido-3-phenylpropanoic acid

Downstream raw materials:

3-{1-[(1S)-1-carboxy-2-phenylethyl]-1H-1,2,3-triazol-4-yl}-L-alanine hydrochloride

C₁₉H₂₄N₄O₆