tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate
• CAS No.: 1613043-90-5
• Molecular Formula: C₅₅H₇₆N₈O₁₁
• Molecular Weight: 1025.26

Synonyms:tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate

Chemical Property of tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate

Chemical Property:

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Technology Process of tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate

There total 8 articles about tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate 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: 81.0%

tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate → tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate (1613043-90-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 19h;

DOI:10.1002/ejoc.201301773

Reference yield:

(S)-benzyl 2-(((S)-2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-3-((tert-butyldiphenylsilyl)-oxy)propyl)(4-methoxybenzyl)amino)-3-methylbutanoate (1613043-85-8) → tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate (1613043-90-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: palladium hydroxide, 20 wt% on carbon; hydrogen / ethanol / 9 h

1.2: 24 h / 20 °C

2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 40 °C

3.1: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 20 °C

5.1: lithium hydroxide / methanol; tetrahydrofuran; water / 13 h / 20 °C

6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 2 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 0 °C

With piperidine; palladium hydroxide, 20 wt% on carbon; tetrabutyl ammonium fluoride; hydrogen; 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 hydroxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201301773

Reference yield:

(S)-methyl 2-((3S,6S)-4-((S)-2-amino-3-(tert-butoxy)propanoyl)-6-(((tert-butyldiphenyl-silyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate → tert-butyl ((S)-1-(((S)-1-(((S)-1-((2S,5S)-4-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(hydroxymethyl)-2-isopropyl-3-oxopiperazin-1-yl)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)amino)-3-(4-(tert-butoxy)phenyl)-1-oxopropan-2-yl)carbamate (1613043-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 20 °C

2: lithium hydroxide / methanol; tetrahydrofuran; water / 13 h / 20 °C

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 2 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 0 °C

With tetrabutyl ammonium fluoride; 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 hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.201301773

upstream raw materials:

Fmoc-Ser(tBu)-OH

(S)-benzyl 2-(((S)-2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-3-((tert-butyldiphenylsilyl)-oxy)propyl)(4-methoxybenzyl)amino)-3-methylbutanoate

(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

(S)-methyl 2-((3S,6S)-4-((6S,9S,12S)-9-benzyl-6-(4-(tert-butoxy)benzyl)-12-(tert-butoxymethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oyl)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

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