(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

Base Information

• Chemical Name: (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
• CAS No.: 132235-86-0
• Molecular Formula: C₄₂H₆₃N₇O₆
• Molecular Weight: 762.006

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (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

There total 11 articles about (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 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: 70.0%

N-<5(S)-amino-4(S)-hydroxy-6-cyclohexyl-2(S)-isopropylhexanoyl>-2(S)-methylbutylamine hydrochloride (124322-07-2) + (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 (132235-85-9) → (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 [(1S,2S,4S)-1-cyclohexylmethyl-2-hydroxy-5-methyl-4-((S)-2-methyl-butylcarbamoyl)-hexyl]-amide (132235-86-0)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/jm00108a006

Reference yield:

N-tert-butyloxycarbonyl-L-prolyl-L-phenylalanine (52071-65-5) → (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 [(1S,2S,4S)-1-cyclohexylmethyl-2-hydroxy-5-methyl-4-((S)-2-methyl-butylcarbamoyl)-hexyl]-amide (132235-86-0)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropylethylamine, diethylphosphoryl cyanide / CH₂Cl₂ / 18 h

2: 100 percent / 1-hydroxybenzotriazole / methanol / 18 h

3: 72 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

4: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 h

5: 78 percent / 4-(dimethylamino)pyridine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 120 h

6: 100 percent / ammonium formate / 5percent Pd/C / dimethylformamide / 18 h

7: 70 percent / 4-(dimethylamino)pyridine, diisopropylethylamine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / dimethylformamide / 18 h

With dmap; diethylphosphoryl cyanide; ammonium formate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00108a006

Reference yield:

Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester (132259-58-6) → (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 [(1S,2S,4S)-1-cyclohexylmethyl-2-hydroxy-5-methyl-4-((S)-2-methyl-butylcarbamoyl)-hexyl]-amide (132235-86-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 h

2: 78 percent / 4-(dimethylamino)pyridine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 120 h

3: 100 percent / ammonium formate / 5percent Pd/C / dimethylformamide / 18 h

4: 70 percent / 4-(dimethylamino)pyridine, diisopropylethylamine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / dimethylformamide / 18 h

With dmap; ammonium formate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00108a006

upstream raw materials:

N-<5(S)-amino-4(S)-hydroxy-6-cyclohexyl-2(S)-isopropylhexanoyl>-2(S)-methylbutylamine hydrochloride

(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

(S)-2-methylbutylamine

N-<4-(S)-<(tert-butyldimethylsilyl)oxy>-5(S)-<(tert-butyloxycarbonyl)amino>-6-cyclohexyl-2(S)-isopropylhexanoyl>-2(S)-methylbutylamine

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