N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide

Base Information

• Chemical Name: N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide
• CAS No.: 1313706-18-1
• Molecular Formula: C₃₂H₄₀N₆O₈
• Molecular Weight: 636.705

Synonyms:N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide

Chemical Property of N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide

Chemical Property:

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Technology Process of N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide

There total 3 articles about N₂,N₅-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide 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: 78.0%

dibenzyl 2,2’-((3,6-diaminopyrazine-2,5-dicarbonyl)bis(azanediyl))(2R,2’R)-bis(3-hydroxypropanoate) (1234369-93-7) + propionaldehyde (123-38-6) → N2,N5-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide (1313706-18-1)

Guidance literature:

dibenzyl 2,2’-((3,6-diaminopyrazine-2,5-dicarbonyl)bis(azanediyl))(2R,2’R)-bis(3-hydroxypropanoate); propionaldehyde; With acetic acid; In 1,2-dichloro-ethane; at 0 ℃; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm200257k

Reference yield:

3,6-diaminopyrazine-2,5-dicarboxylic acid (203798-34-9) → N2,N5-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide (1313706-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 0.25 h / 20 °C / Inert atmosphere; Cooling with ice

1.3: 14 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: acetic acid / 1,2-dichloro-ethane / 0 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With acetic acid; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm200257k

Reference yield:

D-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) → N2,N5-bis[(R)-1-(benzyloxy)-3-hydroxy-1-oxopropan-2-yl]-3,6-bis(propylamino)pyrazine-2,5-dicarboxamide (1313706-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 0.25 h / 20 °C / Inert atmosphere; Cooling with ice

1.3: 14 h / 20 °C / Inert atmosphere; Cooling with ice

2.1: acetic acid / 1,2-dichloro-ethane / 0 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With acetic acid; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm200257k

upstream raw materials:

dibenzyl 2,2’-((3,6-diaminopyrazine-2,5-dicarbonyl)bis(azanediyl))(2R,2’R)-bis(3-hydroxypropanoate)

propionaldehyde

3,6-diaminopyrazine-2,5-dicarboxylic acid

D-serine benzyl ester hydrochloride

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