N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester

Base Information

• Chemical Name: N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester
• CAS No.: 132259-58-6
• Molecular Formula: C₃₈H₄₉N₅O₈
• Molecular Weight: 703.836

Synonyms:N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester

Chemical Property of N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester

There total 3 articles about N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl 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: 72.0%

bromoacetic acid tert-butyl ester (5292-43-3) + Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-L-histidine benzyl ester (132235-83-7) → Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester (132259-58-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 18h;

DOI:10.1021/jm00108a006

Reference yield:

Nα-(tert-butyloxycarbonyl)-Nim-tosyl-L-histidine benzyl ester (132259-57-5) → Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester (132259-58-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.9 g / trifluoroacetic acid / CH₂Cl₂ / 1 h

2: diisopropylethylamine, diethylphosphoryl cyanide / CH₂Cl₂ / 18 h

3: 100 percent / 1-hydroxybenzotriazole / methanol / 18 h

4: 72 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

With diethylphosphoryl cyanide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1021/jm00108a006

Reference yield:

Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-tosyl-L-histidine benzyl ester (132235-82-6) → Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester (132259-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 1-hydroxybenzotriazole / methanol / 18 h

2: 72 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1021/jm00108a006

upstream raw materials:

bromoacetic acid tert-butyl ester

N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-L-histidine benzyl ester

N^α-(tert-butyloxycarbonyl)-N^im-tosyl-L-histidine benzyl ester

N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-tosyl-L-histidine benzyl ester

Downstream raw materials:

(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid

(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester

(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid [(1S,2S,4S)-1-cyclohexylmethyl-2-hydroxy-5-methyl-4-((S)-2-methyl-butylcarbamoyl)-hexyl]-amide

C₄₉H₆₉N₉O₇

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