3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone

Base Information

• Chemical Name: 3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone
• CAS No.: 627535-19-7
• Molecular Formula: C₄₃H₆₂N₆O₉
• Molecular Weight: 807

Synonyms:3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone

Chemical Property of 3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone

Chemical Property:

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Technology Process of 3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone

There total 7 articles about 3,6-bis[3'-N^α-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone 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: 59.4%

(S)-N-Boc-2,6-dimethyltyrosine (99953-00-1,111633-04-6) + 3,6-bis(3'-aminopropyl)-5-methyl-2(1H)-pyrazinone*2AcOH → 3,6-bis[3'-Nα-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone (627535-19-7)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h; pH=8;

DOI:10.1021/jm0304616

Reference yield:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → 3,6-bis[3'-Nα-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone (627535-19-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: isobutyl chloroformate; Et₃N / tetrahydrofuran

1.2: tetrahydrofuran; diethyl ether / 4 °C

1.3: 88.9 percent / aq. HCl / tetrahydrofuran; diethyl ether; dioxane / 0.25 h / -15 °C

2.1: HCl / dioxane

3.1: isobutyl chloroformate; Et₃N / tetrahydrofuran / 0.17 h / cooling

3.2: 43 percent / Et₃N / dimethylformamide / 0 - 20 °C

4.1: HCl / dioxane

5.1: 52.3 percent / methanol / 1 h / Heating

6.1: AcOH; H₂ / Pd black / 1 h

7.1: 59.4 percent / [benzotriazol-1-yloxytris(dimethylamino)phosphonium]PF₆; diisopropylethylamine / dimethylformamide / 4 h / 20 °C / pH 8

With hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0304616

Reference yield:

3,6-bis(3'-benzyloxycarbonylaminopropyl)-5-methyl-2(1H)-pyrazinone (501022-53-3) → 3,6-bis[3'-Nα-Boc-(2',6'-dimethyl-L-tyrosine)aminopropyl]-5-methyl-2(1H)-pyrazinone (627535-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: AcOH; H₂ / Pd black / 1 h

2: 59.4 percent / [benzotriazol-1-yloxytris(dimethylamino)phosphonium]PF₆; diisopropylethylamine / dimethylformamide / 4 h / 20 °C / pH 8

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; palladium; In N,N-dimethyl-formamide;

DOI:10.1021/jm0304616

upstream raw materials:

(S)-N-Boc-2,6-dimethyltyrosine

Z-Orn(Boc)-OH

3,6-bis(3'-benzyloxycarbonylaminopropyl)-5-methyl-2(1H)-pyrazinone

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