N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester
• CAS No.: 112151-86-7
• Molecular Formula: C₄₀H₅₆N₆O₉
• Molecular Weight: 764.919

Synonyms:N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester

Chemical Property of N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Useful:

Technology Process of N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester

There total 5 articles about N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine 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: 75.0%

L-alaninyl-L-phenylalanine methyl ester hydrochloride (2280-75-3) + (3S,4S)-4-[(S)-3-(1-Benzyloxymethyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionylamino]-3-hydroxy-6-methyl-heptanoic acid (112151-89-0) → N-(tert-butyloxycarbonyl)-N?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester (112151-86-7)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 1.) 0 deg C, 3 h, 2.) room temperature, 15 h;

DOI:10.1021/jm00398a022

Reference yield:

N-tert-butyloxycarbonylalanylphenylalanine methyl ester (2280-66-2) → N-(tert-butyloxycarbonyl)-N?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester (112151-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / ethyl acetate / 1 h / -20 °C

2: 75 percent / N-hydroxybenzotriazole, diisopropylethylamine, dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 3 h, 2.) room temperature, 15 h

With hydrogenchloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00398a022

Reference yield:

(3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate (67010-43-9) → N-(tert-butyloxycarbonyl)-N?-imid-<(benzyloxy)methyl>-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester (112151-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / ethyl acetate / 1 h / -20 °C

2: 74 percent / N-hydroxybenzotriazole, diisopropylethylamine, dicyclohexylcarbodiimide / 1.) 0 deg C, 3 h, 2.) room temperature, 15 h

3: 85 percent / aq. NaOH / H₂O; dioxane / 1 h / Ambient temperature

4: 75 percent / N-hydroxybenzotriazole, diisopropylethylamine, dicyclohexylcarbodiimide / dimethylformamide / 1.) 0 deg C, 3 h, 2.) room temperature, 15 h

With hydrogenchloride; sodium hydroxide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00398a022

upstream raw materials:

L-alaninyl-L-phenylalanine methyl ester hydrochloride

(3S,4S)-4-[(S)-3-(1-Benzyloxymethyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionylamino]-3-hydroxy-6-methyl-heptanoic acid

N-tert-butyloxycarbonylalanylphenylalanine methyl ester

(3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate

Downstream raw materials:

N-(tert-butyloxycarbonyl)-N^?-imid-<(benzyloxy)methyl>-L-phenylalanylglycyl-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester

2-amino-L-phenylalanylglycyl-L-histidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-alanyl-L-phenylalanine methyl ester dihydrochloride

(S)-2-((S)-2-{(3S,4S)-4-[(S)-2-Amino-3-(1-benzyloxymethyl-1H-imidazol-4-yl)-propionylamino]-3-hydroxy-6-methyl-heptanoylamino}-propionylamino)-3-phenyl-propionic acid methyl ester; hydrochloride

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