N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

Base Information

• Chemical Name: N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester
• CAS No.: 233266-67-6
• Molecular Formula: C₂₀H₂₃F₅N₂O₆S
• Molecular Weight: 514.47

Synonyms:N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

Chemical Property of N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

There total 4 articles about N^α-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine 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: 77.0%

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester (172749-96-1) + methyl ethyl N-pentafluorophenyl-N-allyloxycarbonyl-aminomethyl sulfonium tetrafluoroborate → Nα-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester (233266-67-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(99)00323-3

Reference yield:

2,3,4,5,6-pentafluoroaniline (771-60-8) → Nα-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester (233266-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C

1.2: 96 percent / tetrahydrofuran / 24 h / 50 °C

2.1: sodium hydride / dimethylformamide

2.2: 2.42 g / dimethylformamide / 2 h / 20 °C

3.1: 76 percent / CH₂Cl₂ / 8 h / 20 °C

4.1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

With ethylmagnesium chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Alkylation / 4.1: Condensation;

DOI:10.1016/S0040-4020(99)00323-3

Reference yield:

N-pentafluorophenyl-carbamic acid allyl ester (233266-56-3) → Nα-tert-butoxycarbonyl-S-[N-(pentafluorophenyl)-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester (233266-67-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / dimethylformamide

1.2: 2.42 g / dimethylformamide / 2 h / 20 °C

2.1: 76 percent / CH₂Cl₂ / 8 h / 20 °C

3.1: 77 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

With sodium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Alkylation / 3.1: Condensation;

DOI:10.1016/S0040-4020(99)00323-3

upstream raw materials:

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester

2,3,4,5,6-pentafluoroaniline

N-pentafluorophenyl-carbamic acid allyl ester

N-pentafluorophenyl-N-methylthiomethyl-carbamic acid allyl ester

Downstream raw materials:

N^α-tert-butoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine methyl ester

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