[N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester

Base Information

• Chemical Name: [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester
• CAS No.: 1091604-26-0
• Molecular Formula: C₁₉H₂₇N₃O₇
• Molecular Weight: 409.439

Synonyms:[N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester

Chemical Property of [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester

Chemical Property:

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Technology Process of [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester

There total 5 articles about [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic 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: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + [((S)-2-Benzyloxycarbonylamino-propionyl)-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-amino]-acetic acid methyl ester (439916-85-5) → [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester (1091604-26-0)

Guidance literature:

[((S)-2-Benzyloxycarbonylamino-propionyl)-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-amino]-acetic acid methyl ester; With pyrrolidine; In tetrahydrofuran; at 20 ℃;

di-tert-butyl dicarbonate; With dmap; In tetrahydrofuran; at 20 ℃;

With methylamine; In tetrahydrofuran; methanol; at 20 ℃; Further stages.;

DOI:10.1016/j.tet.2008.08.087

Reference yield:

C24H35N3O9 (439916-98-0) → [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester (1091604-26-0)

Guidance literature:

With magnesium chlorite; In acetonitrile;

DOI:10.1016/S0040-4039(02)00119-3

Reference yield:

N-benzyloxycarbonylalaninehydrazid (17350-66-2) → [N-(2-benzyloxycarbonylamino-propionyl)-N'-tert-butoxycarbonyl-hydrazino]-acetic acid methyl ester (1091604-26-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / DBAD; PPh₃ / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: MeNH₂ / tetrahydrofuran / 3 h / 20 °C

2.2: 77 percent / DMAP / tetrahydrofuran / 20 °C

3.1: Mg(ClO₂)2 / acetonitrile

With magnesium chlorite; dibenzyl azodicarboxylate; triphenylphosphine; methylamine; In tetrahydrofuran; acetonitrile; 2.1: Mitsunobu reaction;

DOI:10.1016/S0040-4039(02)00119-3

upstream raw materials:

C₂₄H₃₅N₃O₉

N-benzyloxycarbonylalaninehydrazid

[(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

[((S)-2-Benzyloxycarbonylamino-propionyl)-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-amino]-acetic acid methyl ester

Downstream raw materials:

C₁₄H₁₉N₃O₅

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