7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester

Base Information

• Chemical Name: 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester
• CAS No.: 905980-66-7
• Molecular Formula: C₃₃H₃₇N₃O₇
• Molecular Weight: 587.673

Synonyms:7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester

Chemical Property of 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic acid methyl ester

There total 11 articles about 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.0^1,5]undecane-11-carboxylic 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:

2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-2-carboxylic acid methyl ester (905980-61-2) → 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.01,5]undecane-11-carboxylic acid methyl ester (905980-66-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 79 percent / HATU; iPr₂NEt / dimethylformamide

2.1: H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

2.2: 74 percent / toluene / 4 h / Heating

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 72 percent / dimethylformamide / 2 h / 0 °C

4.1: TBAF / tetrahydrofuran / 2 h

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / H₂O / 0.5 h / 20 °C

7.1: 0.45 g / diethyl ether; methanol; benzene

8.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

8.2: 65 percent / Fe(acac)3 / tetrahydrofuran / 0.83 h / -78 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja061660s

Reference yield:

1-benzyl 2-methyl 2-(3'-hydroxypropyl)pyrrolidine-1,2-dicarboxylate (161417-44-3) → 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.01,5]undecane-11-carboxylic acid methyl ester (905980-66-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 100 percent / H₂ / Pd/C / methanol / 3 h

3.1: 79 percent / HATU; iPr₂NEt / dimethylformamide

4.1: H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

4.2: 74 percent / toluene / 4 h / Heating

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 72 percent / dimethylformamide / 2 h / 0 °C

6.1: TBAF / tetrahydrofuran / 2 h

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / H₂O / 0.5 h / 20 °C

9.1: 0.45 g / diethyl ether; methanol; benzene

10.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

10.2: 65 percent / Fe(acac)3 / tetrahydrofuran / 0.83 h / -78 - 20 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja061660s

Reference yield:

2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (905981-10-4) → 7-(1-tert-butoxycarbonyl-1H-indol-3-ylmethyl)-8-(4-methoxy-benzyl)-6,9-dioxo-5,8-diaza-tricyclo[5.2.2.01,5]undecane-11-carboxylic acid methyl ester (905980-66-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / H₂ / Pd/C / methanol / 3 h

2.1: 79 percent / HATU; iPr₂NEt / dimethylformamide

3.1: H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

3.2: 74 percent / toluene / 4 h / Heating

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 72 percent / dimethylformamide / 2 h / 0 °C

5.1: TBAF / tetrahydrofuran / 2 h

6.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

7.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / H₂O / 0.5 h / 20 °C

8.1: 0.45 g / diethyl ether; methanol; benzene

9.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

9.2: 65 percent / Fe(acac)3 / tetrahydrofuran / 0.83 h / -78 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja061660s

upstream raw materials:

2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-2-carboxylic acid methyl ester

1-benzyl 2-methyl 2-(3'-hydroxypropyl)pyrrolidine-1,2-dicarboxylate

2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

N-carbobenzyloxy-L-proline methyl ester

Downstream raw materials:

1-(R)-<methyl>-2,8-diketo-10-(S)-(1-methylethenyl)-9-(4-methoxybenzyl)-3,9-diazatricyclo<5.2.2.0^3,7>undecane

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