(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

Base Information

Chemical Name:(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate
CAS No.:1427722-38-0
Molecular Formula:C₄₁H₄₆N₂O₅
Molecular Weight:646.827
Hs Code.:

Synonyms:(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

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Chemical Property of (-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

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Technology Process of (-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

There total 3 articles about (-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-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:

: 54157-11-8
2-{[(triphenyl)methyl]oxy}ethylamine

: 862499-33-0
tert-butyl 3-(N-Boc-indol-3-yl)propenoate

: 1427722-38-0
(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

: 1427722-39-1
(-)-tert-butyl (R)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

Guidance literature:: 2-{[(triphenyl)methyl]oxy}ethylamine; With n-butyllithium; In hexane; toluene; at -78 ℃; for 0.5h;

tert-butyl 3-(N-Boc-indol-3-yl)propenoate; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In hexane; toluene; at -78 ℃; for 0.7h;

With ammonium chloride; In hexane; water; toluene; Overall yield = 18 %; Overall yield = 57 mg;
DOI:10.1016/j.tet.2013.02.035

Reference yield:

: 862499-33-0
tert-butyl 3-(N-Boc-indol-3-yl)propenoate

: 1427722-36-8
(N-tert-butyldimethylsilyl)[2-(trityloxy)ethyl]amine

: 1427722-38-0
(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

: C₃₀H₄₀N₂O₆

Guidance literature:: (N-tert-butyldimethylsilyl)[2-(trityloxy)ethyl]amine; With n-butyllithium; In hexane; toluene; at -78 ℃; for 0.5h;

tert-butyl 3-(N-Boc-indol-3-yl)propenoate; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In hexane; toluene; at -78 - -40 ℃; for 27h;

With ammonium chloride; In hexane; water; toluene; Overall yield = 25 mg;
DOI:10.1016/j.tet.2013.02.035

Reference yield:

: 54157-11-8
2-{[(triphenyl)methyl]oxy}ethylamine

: 1427722-38-0
(-)-tert-butyl (S)-3-(2-(trityloxy)ethylamino)-3-(1-(tert-butoxycarbonyl)indol-3-yl)propanoate

: C₃₀H₄₀N₂O₆

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; dmap / diethyl ether / 19 h / 0 - 20 °C

2.1: n-butyllithium / hexane; toluene / 0.5 h / -78 °C

2.2: 27 h / -78 - -40 °C

With dmap; n-butyllithium; triethylamine; In diethyl ether; hexane; toluene;
DOI:10.1016/j.tet.2013.02.035