N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine

Base Information

• Chemical Name: N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine
• CAS No.: 130985-46-5
• Molecular Formula: C₅₃H₈₁N₉O₉
• Molecular Weight: 988.281

Synonyms:N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine

Chemical Property of N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine

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Technology Process of N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine

There total 8 articles about N-α--L-phenylalanyl>-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine 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--L-phenylalanyl>-Nα-methyl-L-histydyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>-2-pyridylmethylamine (130985-45-4) → N-α--L-phenylalanyl>-Nα-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine (130985-46-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jm00106a026

Reference yield:

ethyl 3-amino-3-methylbutanoate (85532-42-9) → N-α--L-phenylalanyl>-Nα-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine (130985-46-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / CH₂Cl₂ / 18 h

2: 82 percent / aq. KOH / tetrahydrofuran / 18 h

3: 100 percent / diisopropylethylamine, diethylphosphorocyanate / CH₂Cl₂ / 18 h

4: 80 percent / 1-hydroxybenzotriazole / methanol / 18 h

5: 74 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

With potassium hydroxide; diethyl cyanophosphonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00106a026

Reference yield:

ethyl 3-methylbut-2-enoate (638-10-8) → N-α--L-phenylalanyl>-Nα-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine (130985-46-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / NH₃(gas) / ethanol / 22 h / 80 °C

2: 81 percent / CH₂Cl₂ / 18 h

3: 82 percent / aq. KOH / tetrahydrofuran / 18 h

4: 100 percent / diisopropylethylamine, diethylphosphorocyanate / CH₂Cl₂ / 18 h

5: 80 percent / 1-hydroxybenzotriazole / methanol / 18 h

6: 74 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / Ambient temperature

With potassium hydroxide; diethyl cyanophosphonate; ammonia; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm00106a026

upstream raw materials:

N-α--L-phenylalanyl>-N^α-methyl-L-histydyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>-2-pyridylmethylamine

ethyl 3-methylbut-2-enoate

ethyl 3-amino-3-methylbutanoate

3-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid

Downstream raw materials:

N-α-(β-L-valyl)-L-phenylalanyl-N^α-methyl-L-histidyl>-5(S)-amino-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoyl>-L-isoleucyl>(1-oxo-2-pyridyl)methylamine tris(trifluoroacetate)

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