<4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine

Base Information

• Chemical Name: <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine
• CAS No.: 103346-52-7
• Molecular Formula: C₃₈H₅₃F₂N₇O₈S
• Molecular Weight: 805.944

Synonyms:

Chemical Property of <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine

Chemical Property:

Purity/Quality:

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Technology Process of <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine

There total 9 articles about <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine 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:

(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester (82010-31-9) → <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine (103346-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / oxalyl chloride, Et₃N / CH₂Cl₂ / -78 °C

2: 60 percent / Zn / tetrahydrofuran / 0.5 h / Heating

3: 1 M aq. NaOH / tetrahydrofuran / 2 h

4: 74 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / 48 h

5: CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

6: Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / 15 h

With sodium hydroxide; diethylphosphoryl cyanide; oxalyl dichloride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00160a048

Reference yield:

2-(Aminomethyl)pyridine (3731-51-9) → <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine (103346-52-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / Ambient temperature

2: 100 percent / CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

3: 74 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / 48 h

4: CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

5: Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / 15 h

With diethylphosphoryl cyanide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00160a048

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine (103346-52-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / Ambient temperature

2: 100 percent / CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

3: 74 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / CH₂Cl₂ / 48 h

4: CF₃COOH / CH₂Cl₂ / 1 h / Ambient temperature

5: Et₃N, diethylphosphoryl cyanide / CH₂Cl₂ / 15 h

With diethylphosphoryl cyanide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00160a048

upstream raw materials:

(3R,4S)-4-Amino-2,2-difluoro-3-hydroxy-6-methyl-heptanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide

Boc-His(Tos)-OH

2-(Aminomethyl)pyridine

N-(tert-butyloxycarbonyl)-L-isoleucine

Downstream raw materials:

<4(S)-<<-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine

<4(S)-<<-N^im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine

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