5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione

Base Information

• Chemical Name: 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione
• CAS No.: 179678-76-3
• Molecular Formula: C₁₇H₂₀N₂O₄
• Molecular Weight: 316.357

Synonyms:5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione

Chemical Property of 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione

Chemical Property:

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Technology Process of 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione

There total 4 articles about 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione 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: 22.2%

(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[1-phenyl-meth-(Z)-ylidene]-piperazine-2,6-dione (179678-75-2) → 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione (179678-76-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1021/jo015665d

Reference yield:

1-methoxymethoxy-3S-isobutyl-4-p-methoxybenzylpiperazine-2,6-dione (162715-73-3) → 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione (179678-76-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 °C

1.2: 67.5 percent / 2 h

2.1: DIPEA; DMAP / CH₂Cl₂ / -23 - 20 °C

3.1: 22.2 percent / DDQ / CH₂Cl₂; H₂O

With dmap; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1021/jo015665d

Reference yield:

(3S,5S)-3-((R)-Hydroxy-phenyl-methyl)-5-isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione (179678-74-1) → 5-Isobutyl-1-methoxymethoxy-3-[1-phenyl-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione (179678-76-3)

Guidance literature:

Multi-step reaction with 3 steps

1: DIPEA; DMAP / CH₂Cl₂ / -23 - 20 °C

2: 22.2 percent / DDQ / CH₂Cl₂; H₂O

With dmap; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1021/jo015665d

upstream raw materials:

(S)-3-Isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[1-phenyl-meth-(Z)-ylidene]-piperazine-2,6-dione

1-methoxymethoxy-3S-isobutyl-4-p-methoxybenzylpiperazine-2,6-dione

(3S,5S)-3-((R)-Hydroxy-phenyl-methyl)-5-isobutyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione

Methanesulfonic acid (R)-[(2S,6S)-6-isobutyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-phenyl-methyl ester

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