3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Base Information

• Chemical Name: 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester
• CAS No.: 507276-78-0
• Molecular Formula: C₂₀H₃₁NO₅
• Molecular Weight: 365.47

Synonyms:3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Chemical Property of 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

Chemical Property:

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Technology Process of 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

There total 2 articles about 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric 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: 100.0%

methanol (67-56-1) + [1-(4-tert-butoxybenzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butyl ester (507276-76-8) → 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (507276-78-0)

Guidance literature:

With silver benzoate; triethylamine; for 1.25h;

DOI:10.1021/ol027237f

Reference yield:

Boc-Tyr(t-Bu)-OH (47375-34-8) → 3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (507276-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutylchloroformate; N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C

1.2: 85 percent / tetrahydrofuran; diethyl ether / 0.5 h / -20 °C

2.1: 100 percent / PhCO₂Ag; NEt₃ / 1.25 h

With 4-methyl-morpholine; silver benzoate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; 1.2: Arndt-Eistert homologation;

DOI:10.1021/ol027237f

Reference yield: 43.0%

3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester (507276-78-0) → [1-(4-tert-butoxybenzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester (565430-84-4)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1021/ol027237f

upstream raw materials:

methanol

[1-(4-tert-butoxybenzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butyl ester

Boc-Tyr(t-Bu)-OH

Downstream raw materials:

[1-(4-tert-butoxybenzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester

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