(1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid

Base Information

• Chemical Name: (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid
• CAS No.: 74297-57-7
• Molecular Formula: C₅₃H₆₈N₁₀O₁₂
• Molecular Weight: 1037.18

Synonyms:

Chemical Property of (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid

There total 3 articles about (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid 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:

2-({(2S,5R,8S,11S,14S,19S)-19-Amino-2-benzyl-11-(1-hydroxy-ethyl)-5-(1H-indol-3-ylmethyl)-3,6,9,12,20-pentaoxo-8-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-1,4,7,10,13-pentaaza-cycloicosane-14-carbonyl}-amino)-7-azidocarbonyl-heptanoic acid → (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid (74297-57-7,75172-52-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; Yield given; 1.) -20 deg C (18 h), 2.) 5 deg C (72 h);

DOI:10.1021/ja00541a025

Reference yield:

2-({(2S,5R,8S,11S,14S,19S)-19-Amino-2-benzyl-11-(1-hydroxy-ethyl)-5-(1H-indol-3-ylmethyl)-3,6,9,12,20-pentaoxo-8-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-1,4,7,10,13-pentaaza-cycloicosane-14-carbonyl}-amino)-octanedioic acid 8-methyl ester (75172-50-8) → (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid (74297-57-7,75172-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NH₂NH₂, DMF / 1 h / Ambient temperature

2: isoamyl nitrite, HCl / tetrahydrofuran; dimethylformamide / 1 h / -25 °C

3: DIPEA, pH 7.0 / dimethylformamide / 1.) -20 deg C (18 h), 2.) 5 deg C (72 h)

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; hydrazine; isopentyl nitrite; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00541a025

Reference yield:

2-({(2S,5R,8S,11S,14S,19S)-19-Amino-2-benzyl-11-(1-hydroxy-ethyl)-5-(1H-indol-3-ylmethyl)-3,6,9,12,20-pentaoxo-8-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-1,4,7,10,13-pentaaza-cycloicosane-14-carbonyl}-amino)-7-hydrazinocarbonyl-heptanoic acid (75172-51-9) → (1S,4S,7S,10R,13S,16S)-13-Benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-7-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid (74297-57-7,75172-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: isoamyl nitrite, HCl / tetrahydrofuran; dimethylformamide / 1 h / -25 °C

2: DIPEA, pH 7.0 / dimethylformamide / 1.) -20 deg C (18 h), 2.) 5 deg C (72 h)

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; isopentyl nitrite; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00541a025

upstream raw materials:

2-({(2S,5R,8S,11S,14S,19S)-19-Amino-2-benzyl-11-(1-hydroxy-ethyl)-5-(1H-indol-3-ylmethyl)-3,6,9,12,20-pentaoxo-8-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-1,4,7,10,13-pentaaza-cycloicosane-14-carbonyl}-amino)-octanedioic acid 8-methyl ester

2-({(2S,5R,8S,11S,14S,19S)-19-Amino-2-benzyl-11-(1-hydroxy-ethyl)-5-(1H-indol-3-ylmethyl)-3,6,9,12,20-pentaoxo-8-[4-(pyridin-4-ylmethoxycarbonylamino)-butyl]-1,4,7,10,13-pentaaza-cycloicosane-14-carbonyl}-amino)-7-hydrazinocarbonyl-heptanoic acid

Downstream raw materials:

(1S,4S,7S,10R,13S,16S)-7-(4-Amino-butyl)-13-benzyl-4-(1-hydroxy-ethyl)-10-(1H-indol-3-ylmethyl)-3,6,9,12,15,18,26-heptaoxo-2,5,8,11,14,17,25-heptaaza-bicyclo[14.10.4]triacontane-24-carboxylic acid

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