methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate

Base Information

• Chemical Name: methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate
• CAS No.: 937276-25-0
• Molecular Formula: C₁₈H₂₇N₃O₆
• Molecular Weight: 381.429

Synonyms:methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate

Chemical Property of methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate

Chemical Property:

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Technology Process of methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate

There total 4 articles about methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]glycinate 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: 54.0%

Nβ-(benzyloxycarbonyl)-Nα-(tert-butoxycarbonyl)-Nβ-(formylmethyl)hydrazide (192725-92-1) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → methyl N-[2-(Nβ-benzyloxycarbonyl-Nα-tert-butoxycarbonyl-hydrazino)ethyl]glycinate (937276-25-0)

Guidance literature:

N^β-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-N^β-(formylmethyl)hydrazide; glycine ethyl ester hydrochloride; In methanol; at 0 ℃; for 0.25h;

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 3.5h; Further stages.;

DOI:10.1016/j.tet.2007.02.102

Reference yield:

Nβ-(benzyloxycarbonyl)-Nα-(tert-butoxycarbonyl)-Nβ-(2-hydroxyethyl)hydrazide (937276-28-3) → methyl N-[2-(Nβ-benzyloxycarbonyl-Nα-tert-butoxycarbonyl-hydrazino)ethyl]glycinate (937276-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 2.5 h / 20 °C

1.2: 88 percent / methyl tert-butyl ether; NaHCO₃; Na₂S₂O₃ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

2.1: methanol / 0.25 h / 0 °C

2.2: 54 percent / NaBH₃CN; AcOH / methanol / 3.5 h / 20 °C

With Dess-Martin periodane; In methanol; dichloromethane; water;

DOI:10.1016/j.tet.2007.02.102

Reference yield:

Nβ-(benzyloxycarbonyl)-Nβ-(2-hydroxyethyl)hydrazide (316802-29-6) → methyl N-[2-(Nβ-benzyloxycarbonyl-Nα-tert-butoxycarbonyl-hydrazino)ethyl]glycinate (937276-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71.3 percent / triethylamine / tetrahydrofuran / 3 h / 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 2.5 h / 20 °C

2.2: 88 percent / methyl tert-butyl ether; NaHCO₃; Na₂S₂O₃ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

3.1: methanol / 0.25 h / 0 °C

3.2: 54 percent / NaBH₃CN; AcOH / methanol / 3.5 h / 20 °C

With Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.tet.2007.02.102

upstream raw materials:

N^β-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-N^β-(formylmethyl)hydrazide

glycine ethyl ester hydrochloride

N^β-(benzyloxycarbonyl)-N^β-(2-hydroxyethyl)hydrazide

N^β-(benzyloxycarbonyl)-N^α-(tert-butoxycarbonyl)-N^β-(2-hydroxyethyl)hydrazide

Downstream raw materials:

methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonyl-hydrazino)ethyl]-N-[(thymin-1-yl)acetyl]glycinate

methyl N-[2-(N^β-benzyloxycarbonyl-N^α-tert-butoxycarbonylhydrazino)ethyl]-N-{[4-N-(benzyloxycarbonyl)cytosin-1-yl]acetyl}glycinate

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