L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate

Base Information

• Chemical Name: L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate
• CAS No.: 132259-60-0
• Molecular Formula: C₂HF₃O₂*C₂₉H₃₃N₅O₆
• Molecular Weight: 661.635

Synonyms:L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate

Chemical Property of L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate

Chemical Property:

Purity/Quality:

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Technology Process of L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate

There total 2 articles about L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate 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:

Nα-(tert-butyloxycarbonyl)-Nim-tosyl-L-histidine benzyl ester (132259-57-5) → L-prolyl-L-phenylalanyl-Nim-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate (132259-60-0)

Guidance literature:

Multi-step reaction with 5 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

5: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 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) → L-prolyl-L-phenylalanyl-Nim-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate (132259-60-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 72 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

3: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 h

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

DOI:10.1021/jm00108a006

Reference yield: 78.0%

L-prolyl-L-phenylalanyl-Nim-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate (132259-60-0) → (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.04,8]nonadeca-16(19),17-diene-14-carboxylic acid benzyl ester (132235-84-8)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; for 120h;

DOI:10.1021/jm00108a006

upstream raw materials:

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 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

(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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