(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate

Base Information

• Chemical Name: (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate
• CAS No.: 503416-73-7
• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.362

Synonyms:(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate

Chemical Property of (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate

There total 9 articles about (S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(hydroxy)phenylalanine carboxylate 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: 99.0%

(S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(benzyloxy)phenylalanine carboxylate (503416-72-6) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(hydroxy)phenylalanine carboxylate (503416-73-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; under 2584 Torr;

DOI:10.1016/S0040-4039(02)02035-X

Reference yield:

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate (37169-36-1) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(hydroxy)phenylalanine carboxylate (503416-73-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / potassium carbonate; sodium iodide; n-Bu₄N⁽¹⁺⁾*Br^(1-) / acetone / 4 h / Heating

2: 97 percent / sodium hydroxide / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

3: triethylamine / tetrahydrofuran / -15 - 0 °C

4: 5.94 g / tetrahydrofuran; diethyl ether / 18 h / 20 °C

5: 61 percent / silver(I) benzoate; triethylamine / tetrahydrofuran / 3 h / 20 °C

6: 95 percent / hydrogen / Pd/C / methanol; tetrahydrofuran / 18 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; hydrogen; silver benzoate; potassium carbonate; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; acetone; 5: Arndt-Eistert homologation;

DOI:10.1016/j.tetasy.2004.11.089

Reference yield:

3-[3,4-di(benzyloxy)phenyl]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid (59727-98-9) → (S)-methyl N-(tert-butyloxycarbonyl)-β3-homo-3,4-bis(hydroxy)phenylalanine carboxylate (503416-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / tetrahydrofuran / -15 - 0 °C

2: 5.94 g / tetrahydrofuran; diethyl ether / 18 h / 20 °C

3: 61 percent / silver(I) benzoate; triethylamine / tetrahydrofuran / 3 h / 20 °C

4: 95 percent / hydrogen / Pd/C / methanol; tetrahydrofuran / 18 h / 20 °C

With hydrogen; silver benzoate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; 3: Arndt-Eistert homologation;

DOI:10.1016/j.tetasy.2004.11.089

upstream raw materials:

(S)-methyl N-(tert-butyloxycarbonyl)-β³-homo-3,4-bis(benzyloxy)phenylalanine carboxylate

di-tert-butyl dicarbonate

levodopa

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate

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