(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

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Chemical Name:(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide
CAS No.:1273503-96-0
Molecular Formula:C₃₇H₅₂F₃N₃O₃Sn
Molecular Weight:762.543
Hs Code.:

Synonyms:(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

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Chemical Property of (2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

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Technology Process of (2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

There total 2 articles about (2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide 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: 92.0%

: 291527-20-3
ethyl (2-(tributylstannyl)allyl) carbonate

: 1273503-15-3
(S)-2-(2,2,2-trifluoroacetamido)-N-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl]-3-phenylpropanamide

: 1273503-96-0
(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

Guidance literature:: With ZnCl₂; [PdCl(C₃H₅)]2; n-butyllithium; In tetrahydrofuran; (under N2); n-BuLi added to soln. of HMDS in THF at -20°C, stirred for 20 min, then 10 min, cooled to -78°C, mixt. of ligand, ZnCl2 in THF added, stirred for 30 min, Pd-catalyst, PPh3 in THF added, Sn-compound added, stirred overnight; diluted with EtOAc, KHSO4 added, extd. with EtOAc, dried over Na2SO4, concd. in vacuo, silica gel column chromy. with hexane/EtOAc 4:1;
DOI:10.1039/c0ob00628a

Reference yield:

: 291527-20-3
ethyl (2-(tributylstannyl)allyl) carbonate

: 1273503-15-3
(S)-2-(2,2,2-trifluoroacetamido)-N-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl]-3-phenylpropanamide

: 1273503-96-0
(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

: 1448522-31-3
N-(trifluoroacetyl)-(S)-phenylalanyl-(R)-[2-(tributylstannyl)allyl]glycine 3,4-dihydroquinolinide

Guidance literature:: (S)-2-(2,2,2-trifluoroacetamido)-N-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl]-3-phenylpropanamide; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

ethyl (2-(tributylstannyl)allyl) carbonate; With bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h; Overall yield = 92 %; Overall yield = 102 mg; stereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0033-1338477

Reference yield: 91.0%

: 1273503-96-0
(2S)-2-(2,2,2-trifluoroacetamido)-N-[4-(tributylstannyl)-1-(3,4-dihydroquinolin-1(2H)-yl)-1-oxopent-4-en-2-yl]-3-phenylpropanamide

: 1273504-05-4
(2S)-2-(2,2,2-trifluoroacetamido)-N-[1-(3,4-dihydroquinolin-1(2H)-yl)-4-iodo-1-oxopent-4-en-2-yl]-3-phenylpropanamide

Guidance literature:: With iodine; In diethyl ether; for 0.5h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1039/c0ob00628a