(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Base Information

Chemical Name:(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate
CAS No.:1596359-59-9
Molecular Formula:C₂₈H₃₁NO₂
Molecular Weight:413.56
Hs Code.:

Synonyms:(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

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Chemical Property of (Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

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Technology Process of (Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

There total 4 articles about (Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate 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: 60.0%

: 4088-60-2,542-72-3
cis-2-buten-1-ol

: 265669-72-5
tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

: 1596359-59-9
(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Guidance literature:: tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Inert atmosphere;

cis-2-buten-1-ol; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c4ob00274a

Reference yield:

: 504-61-0,542-72-3
(E)-but-2-enol

: 265669-72-5
tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

: 1596359-51-1
(E)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

: 1596359-59-9
(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Guidance literature:: tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Inert atmosphere;

(E)-but-2-enol; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; Overall yield = 62 %; Overall yield = 613 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c4ob00274a

Reference yield:

: lithium N-benzyl-N-((S)-1-phenylethyl)amide

: 1596359-59-9
(Z)-but-2′-en-1′-yl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.2: 1 h / 0 - 20 °C / Inert atmosphere

2.3: 16 h / 0 - 20 °C / Inert atmosphere

With trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4ob00274a