(phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine

Base Information

• Chemical Name: (phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine
• CAS No.: 126082-58-4
• Molecular Formula: C₄₅H₆₁N₇O₇S
• Molecular Weight: 844.088

Synonyms:(phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine

Chemical Property of (phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine

Chemical Property:

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Technology Process of (phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine

There total 4 articles about (phenylacetyl)-N^im-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-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: 86.0%

phenylacetic acid (103-82-2) + (2S,4S,5S)-5-{(S)-2-Amino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-4-hydroxy-2-isopropyl-7-methyl-octanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide (103372-31-2) → (phenylacetyl)-Nim-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine (126082-58-4)

Guidance literature:

With diethylphosphoryl cyanide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00167a009

Reference yield:

N-α-<4(S)-<(tert-butyldimethylsilyl)oxy>-5(S)-<(tert-butyloxycarbonyl)amino>-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine (103372-32-3) → (phenylacetyl)-Nim-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine (126082-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl (gas) / diethyl ether / 0.25 h

2: diethylphosphoryl cyanide (DEPC), Et₃N / CH₂Cl₂

3: 50 mg / trifluoroacetic acid (TFA) / CH₂Cl₂ / 0.75 h

4: 86 percent / diisopropylethylamine, diethylphosphoryl cyanide (DEPC) / CH₂Cl₂; dimethylformamide / Ambient temperature

With hydrogenchloride; diethylphosphoryl cyanide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00167a009

Reference yield:

(2S,4S,5S)-5-Amino-4-hydroxy-2-isopropyl-7-methyl-octanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide; hydrochloride (103882-43-5,123537-40-6) → (phenylacetyl)-Nim-tosyl-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine (126082-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: diethylphosphoryl cyanide (DEPC), Et₃N / CH₂Cl₂

2: 50 mg / trifluoroacetic acid (TFA) / CH₂Cl₂ / 0.75 h

3: 86 percent / diisopropylethylamine, diethylphosphoryl cyanide (DEPC) / CH₂Cl₂; dimethylformamide / Ambient temperature

With diethylphosphoryl cyanide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00167a009

upstream raw materials:

phenylacetic acid

(2S,4S,5S)-5-{(S)-2-Amino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-4-hydroxy-2-isopropyl-7-methyl-octanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide

N-α-<4(S)-<(tert-butyldimethylsilyl)oxy>-5(S)-<(tert-butyloxycarbonyl)amino>-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine

(2S,4S,5S)-5-Amino-4-hydroxy-2-isopropyl-7-methyl-octanoic acid {(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide; hydrochloride

Downstream raw materials:

(phenylacetyl)-L-histidyl-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-(methyloctanoyl)-L-isoleucyl-2-pyridylmethylamine

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