methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

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Chemical Name:methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate
CAS No.:1533429-96-7
Molecular Formula:C₂₄H₂₃N₃O₅S
Molecular Weight:465.53
Hs Code.:

Synonyms:methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

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Chemical Property of methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

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Technology Process of methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

There total 11 articles about methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate 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: 79.0%

: 1533429-80-9
methyl (S)-2-Amino-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

: 108-24-7
acetic anhydride

: 1533429-96-7
methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol403429e

Reference yield:

: 233-84-1
1H-pyrrolo[3,2-c]isoquinoline

: 1533429-96-7
methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: hexamethylenetetramine / water / Inert atmosphere; Reflux

2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C

4.1: triethylamine; thionyl chloride / dichloromethane / -10 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 20 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; hexamethylenetetramine; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol403429e

Reference yield:

: 271784-16-8
4-amino-3-acetylenetrimethylsililisoquinoline

: 1533429-96-7
methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium amide / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere

2.1: hexamethylenetetramine / water / Inert atmosphere; Reflux

3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C

5.1: triethylamine; thionyl chloride / dichloromethane / -10 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; hexamethylenetetramine; sodium hydride; sodium amide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol403429e