N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester
• CAS No.: 112151-85-6
• Molecular Formula: C₂₉H₄₄N₄O₇
• Molecular Weight: 560.691

Synonyms:N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester

Chemical Property of N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester

Chemical Property:

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Technology Process of N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester

There total 2 articles about N-(tert-butyloxycarbonyl)-N^?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl 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: 74.0%

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine (83468-83-1) + (S,S)-Sta-OEt hydrochloride (84851-46-7) → N-(tert-butyloxycarbonyl)-N?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester (112151-85-6)

Guidance literature:

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

DOI:10.1021/jm00398a022

Reference yield:

(3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate (67010-43-9) → N-(tert-butyloxycarbonyl)-N?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester (112151-85-6)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jm00398a022

Reference yield: 85.0%

N-(tert-butyloxycarbonyl)-N?-imid-(benzyloxymethyl)-L-hystidyl-4(S)-amino-3(S)-hydroxy-6-methylheptanoic acid ethyl ester (112151-85-6) → (3S,4S)-4-[(S)-3-(1-Benzyloxymethyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionylamino]-3-hydroxy-6-methyl-heptanoic acid (112151-89-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 1h; Ambient temperature;

DOI:10.1021/jm00398a022

upstream raw materials:

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine

(S,S)-Sta-OEt hydrochloride

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

Downstream raw materials:

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

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

(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

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

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