(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

Base Information

Chemical Name:(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile
CAS No.:927385-54-4
Molecular Formula:C₂₂H₂₈N₂O
Molecular Weight:336.477
Hs Code.:

Synonyms:(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

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Chemical Property of (S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

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Technology Process of (S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

There total 3 articles about (S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile 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: 77.0%

: 927385-43-1
(S)-[4-(prop-2-ynyloxy)pent-1-ynyl]benzene

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 14278-96-7
3-(isobutylamino)propionitrile

: 927385-54-4
(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

Guidance literature:: formaldehyd; 3-(isobutylamino)propionitrile; With o-toluenesulfonic acid; In dichloromethane; at 60 ℃; for 24h;

(S)-[4-(prop-2-ynyloxy)pent-1-ynyl]benzene; With copper(I) bromide; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃; for 48h; Further stages.;
DOI:10.1021/ol0625280

Reference yield:

: 927385-39-5
(S)-5-phenylpent-4-yn-2-ol

: 927385-54-4
(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: 77 percent / NaH / tetrahydrofuran / 0 - 20 °C

2.1: toluenesulfonic acid / CH₂Cl₂ / 24 h / 60 °C

2.2: 77 percent / CuBr / tetrahydrofuran; dimethylformamide / 48 h / 70 °C

With o-toluenesulfonic acid; sodium hydride; In tetrahydrofuran; dichloromethane; 2.1: alkynyl Mannich reaction;
DOI:10.1021/ol0625280

Reference yield:

: 536-74-3
phenylacetylene

: 927385-54-4
(S)-3-[N-(2-methylpropyl)-[N-4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl]amino]propanenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran / 0.25 h / -78 °C

1.3: 81 percent / tetrahydrofuran / 3 h / -78 °C

2.1: 77 percent / NaH / tetrahydrofuran / 0 - 20 °C

3.1: toluenesulfonic acid / CH₂Cl₂ / 24 h / 60 °C

3.2: 77 percent / CuBr / tetrahydrofuran; dimethylformamide / 48 h / 70 °C

With n-butyllithium; o-toluenesulfonic acid; sodium hydride; In tetrahydrofuran; dichloromethane; 3.1: alkynyl Mannich reaction;
DOI:10.1021/ol0625280