methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

Base Information

Chemical Name:methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate
CAS No.:1261352-28-6
Molecular Formula:C₂₁H₂₈N₄O₆
Molecular Weight:432.477
Hs Code.:

Synonyms:methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

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Chemical Property of methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

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Technology Process of methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

There total 5 articles about methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate 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: 92.0%

: 116911-32-1
(S)-2-azido-3-phenylpropionic acid methyl ester

: 71460-02-1,173306-82-6
methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate

: 1261352-28-6
methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

Guidance literature:: With pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; for 3h; Reflux; Inert atmosphere;
DOI:10.1016/j.bmcl.2010.09.139

Reference yield:

: 63-91-2,25191-15-5,658-69-5,67675-33-6
L-phenylalanine

: 1261352-28-6
methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

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: pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride / tetrahydrofuran / 3 h / Reflux; Inert atmosphere

With thionyl chloride; copper(ll) sulfate pentahydrate; pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride; triflic azide; triethylamine; In tetrahydrofuran; water; acetonitrile; 3: Huisgen Cycloaddition;
DOI:10.1016/j.bmcl.2010.09.139

Reference yield:

: 23235-01-0
(2S)-2-amino-4-pentynoic acid

: 1261352-28-6
methyl N-(tert-butoxycarbonyl)-3-{1-[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-1H-1,2,3-triazol-5-yl}-L-alaninate

Guidance literature:: Multi-step reaction with 3 steps

1: thionyl chloride / 2.25 h / 0 °C / Reflux

2: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 0 - 20 °C

3: pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride / tetrahydrofuran / 3 h / Reflux; Inert atmosphere

With thionyl chloride; pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; water; 3: Huisgen Cycloaddition;
DOI:10.1016/j.bmcl.2010.09.139