(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

Base Information

Chemical Name:(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one
CAS No.:885971-66-4
Molecular Formula:C₁₉H₂₂N₂O₂S₂
Molecular Weight:374.528
Hs Code.:

Synonyms:(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

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Chemical Property of (-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

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Technology Process of (-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

There total 1 articles about (-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one 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%

: 885971-59-5
5-acetoxy N-crotyl pyyrolidine-2-one

: (4R)-N-acetyl-4-phenyl-1,3-thiazolidine-2-thione

: 885971-66-4
(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

Guidance literature:: (4R)-N-acetyl-4-phenyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30 ℃;

5-acetoxy N-crotyl pyyrolidine-2-one; In dichloromethane; at 0 ℃; for 6h;
DOI:10.1021/jo052364l

Reference yield: 74.0%

: 885971-66-4
(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

: 104-55-2
3-phenyl-propenal

: (S)-1-((E)-But-2-enyl)-5-[(E)-(1R,2R)-2-hydroxy-4-phenyl-1-((R)-4-phenyl-2-thioxo-thiazolidine-3-carbonyl)-but-3-enyl]-pyrrolidin-2-one

Guidance literature:: With chloro-trimethyl-silane; triethylamine; magnesium bromide; In ethyl acetate; at 20 ℃; for 36h;
DOI:10.1021/jo052364l

Reference yield:

: 885971-66-4
(-)-5(S)-2[2-(4(R)-phenyl-2-thioxo-thiazolidine-3-yl)-2-oxo-ethyl]-1-(but-2-enyl)-pyrrolidine-2-one

: 885972-21-4
(S)-1-((E)-But-2-enyl)-5-[(2R,3R)-5-hydroxy-2-((E)-styryl)-tetrahydro-furan-3-yl]-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / triethylamine; TMSCl / MgBr₂*OEt₂ / ethyl acetate / 36 h / 20 °C

2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

3: 96 percent / NaBH₄ / ethanol / 4 °C

4: 90 percent / 4-methylmorpholine N-oxide / TPAP / CH₂Cl₂ / 1 h / 20 °C

5: 76 percent / NaHMDS / tetrahydrofuran / 3 h / -78 °C

6: 88 percent / p-TsOH / tetrahydrofuran; H₂O / 4 h / Heating

With 2,6-dimethylpyridine; sodium tetrahydroborate; chloro-trimethyl-silane; sodium hexamethyldisilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; tetrapropylammonium perruthennate; magnesium bromide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 5: Wittig reaction;
DOI:10.1021/jo052364l