5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester

Base Information

• Chemical Name: 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester
• CAS No.: 1067639-88-6
• Molecular Formula: C₂₈H₂₆N₂O₇
• Molecular Weight: 502.524

Synonyms:5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester

Chemical Property of 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester

Chemical Property:

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Technology Process of 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester

There total 2 articles about 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl 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: 61.0%

N-hydroxyphthalimide (524-38-9) + 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester → 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester (1067639-88-6)

Guidance literature:

N-hydroxyphthalimide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1055/s-2008-1078600

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester (1067639-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; isobutyl chloroformate / tetrahydrofuran / -15 °C / Inert atmosphere

1.2: 0.17 h / -15 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

3.2: 48 h / 0 - 20 °C / Inert atmosphere

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c1cc12010g

Reference yield:

5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-N-[(phenylmethoxy)carbonyl]-L-norvaline phenylmethyl ester (1067639-88-6) → C20H24N2O5

Guidance literature:

With methylhydrazine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1055/s-2008-1078600

upstream raw materials:

N-hydroxyphthalimide

Cbz-(L)-Glu-OBn

Downstream raw materials:

C₃₉H₃₇ClN₂O₅

C₃₉H₃₅ClN₂O₅

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