N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester

Base Information

• Chemical Name: N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester
• CAS No.: 1268691-62-8
• Molecular Formula: C₃₉H₅₇N₅O₆
• Molecular Weight: 691.911

Synonyms:N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester

Chemical Property of N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester

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Technology Process of N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester

There total 3 articles about N₂-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N₅,N₅-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester 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: 85.0%

(2R,5S)-(6-ethoxy-5-isopropyl-2-methyl-3-oxo-2,3,4,5-tetrahydro-pyrazin-2-yl)-acetic acid (908298-93-1) + N5,N5-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester dihydrochloride → N2-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N5,N5-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester (1268691-62-8)

Guidance literature:

With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/hlca.201000202

Reference yield:

(3S,6S)-1-benzyl-3-methyl-3-(3-dibenzylaminopropyl)-5-ethoxy-1,6-dihydro-6-isopropylpyrazin-2-(3H)-one (1005192-75-5) → N2-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N5,N5-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester (1268691-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonia; lithium / tetrahydrofuran; tert-butyl alcohol / 0.08 h / -78 °C / Inert atmosphere

2: hydrogenchloride / ethanol; water / 12 h / 20 °C

3: triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / tetrahydrofuran / 12 h / 20 °C

With hydrogenchloride; ammonia; lithium; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; ethanol; water; tert-butyl alcohol; 1: Birch reduction;

DOI:10.1002/hlca.201000202

Reference yield:

(3S,6S)-3-[3-(dibenzylamino)propyl]-5-ethoxy-3,6-dihydro-6-isopropyl-3-methylpyrazin-2(1H)-one (1268691-58-2) → N2-{2-[(2R,5S)-6-ethoxy-2,3,4,5-tetrahydro-2-methyl-5-isopropyl-3-oxopyrazin-2-yl]acetyl}-N5,N5-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester (1268691-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / ethanol; water / 12 h / 20 °C

2: triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / tetrahydrofuran / 12 h / 20 °C

With hydrogenchloride; triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; ethanol; water;

DOI:10.1002/hlca.201000202

upstream raw materials:

(2R,5S)-(6-ethoxy-5-isopropyl-2-methyl-3-oxo-2,3,4,5-tetrahydro-pyrazin-2-yl)-acetic acid

(3S,6S)-1-benzyl-3-methyl-3-(3-dibenzylaminopropyl)-5-ethoxy-1,6-dihydro-6-isopropylpyrazin-2-(3H)-one

(3S,6S)-3-[3-(dibenzylamino)propyl]-5-ethoxy-3,6-dihydro-6-isopropyl-3-methylpyrazin-2(1H)-one

Downstream raw materials:

N2-acetyl-N-[(1S)-1-(ethoxycarbonyl)-2-methylpropyl]-2-methyl-D-α-asparaginyl-N5,N5-dibenzyl-2-methyl-L-ornithyl-L-valine ethyl ester

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