4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester

Base Information

• Chemical Name: 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester
• CAS No.: 1323407-39-1
• Molecular Formula: C₂₂H₂₃ClN₂O₅
• Molecular Weight: 430.888

Synonyms:4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester

Chemical Property of 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester

Chemical Property:

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Technology Process of 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester

There total 11 articles about 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl 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: 92.0%

4-carbamoyl-4-(4-hydroxy-1-oxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester (1323407-16-4) + 4-(hydroxymethyl)benzyl chloride (16473-35-1) → 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester (1323407-39-1)

Guidance literature:

4-carbamoyl-4-(4-hydroxy-1-oxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester; With di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

4-(hydroxymethyl)benzyl chloride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b01928

Reference yield:

methyl 4,5-diamino-5-oxo-pentanoate hydrochloride (1323290-64-7) → 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester (1323407-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere

2.2: 0.17 h / 20 °C / Inert atmosphere

3.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.9b01928

Reference yield:

3-hydroxy 2-methylbenzoic acid (603-80-5) → 4-carbamoyl-4-[4-(4-chloromethylbenzyloxy)-1-oxo-1,3-dihydroisoindol-2-yl]butyric acid methyl ester (1323407-39-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sulfuric acid / 17 h / 65 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 1 h / 25 °C / Inert atmosphere

3.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / ethyl acetate / 2 h / 65 °C / Inert atmosphere; Irradiation

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 60 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide; water / 15 h / 15 °C / Inert atmosphere

5.2: 0.17 h / 20 °C / Inert atmosphere

6.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6.2: 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; sulfuric acid; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.9b01928

upstream raw materials:

methyl 4,5-diamino-5-oxo-pentanoate hydrochloride

3-hydroxy 2-methylbenzoic acid

methyl 3-hydroxy-2-methylbenzoate

3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-benzoic acid methyl ester

Downstream raw materials:

methyl 5-amino-4-(4-(4-((4,4-dimethylpiperidin-1-yl)methyl)benzyloxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate

4-amino-1-{4-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-yloxymethyl]-benzyl}-pyridinium formate

3-[4-(4-ethylaminomethyl-benzyloxy)-1-oxo-1,3-dihydro-isoindol-2-yl]-piperidine-2,6-dione hydrochloride

3-(4-{4-[(Methyl-phenyl-amino)-methyl]-benzyloxy}-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione

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