(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

Base Information

Chemical Name:(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide
CAS No.:1428248-55-8
Molecular Formula:C₂₆H₃₅ClN₄O₄Si
Molecular Weight:531.127
Hs Code.:

Synonyms:(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

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Chemical Property of (S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

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Technology Process of (S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

There total 7 articles about (S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide 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:

: C₄₁H₄₅ClN₄O₆Si

: 1428248-55-8
(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1016/j.bmc.2013.01.020

Reference yield:

: C₉H₉ClN₂O₃

: 1428248-55-8
(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

Guidance literature:: Multi-step reaction with 4 steps

1: acetic acid; sodium cyanoborohydride / methanol / 2.5 h / Reflux

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C / Cooling

3: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1.5 h / 20 °C

With sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmc.2013.01.020

Reference yield:

: 89639-98-5
(2-chloro-3-nitrophenyl)methanol

: 1428248-55-8
(S)-2-amino-N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chloro-3-nitrobenzyl)-3-(1H-indol-3-yl)propanamide

Guidance literature:: Multi-step reaction with 6 steps

1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane

2: acetic acid / methanol / 0.17 h

3: acetic acid; sodium cyanoborohydride / methanol / 2.5 h / Reflux

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C / Cooling

5: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1.5 h / 20 °C

With oxalyl dichloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: |Swern Oxidation / 1: |Swern Oxidation;
DOI:10.1016/j.bmc.2013.01.020