(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one
CAS No.:1449117-92-3
Molecular Formula:C₃₂H₃₁BrN₂O₆S
Molecular Weight:651.578
Hs Code.:

Synonyms:(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

There total 1 articles about (S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-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: 81.5%

: C₁₆H₁₉NO₃

: 181271-32-9
4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde

: 1449117-92-3
(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: C₁₆H₁₉NO₃; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde; In 1-methyl-pyrrolidin-2-one; dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol4019562

Reference yield: 93.86%

: 1449117-92-3
(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

: 1449117-93-4
(S)-2-((S)-(4-bromo-1-tosyl-1H-indol-3-yl)(hydroxy)methyl)but-3-enehydrazide

Guidance literature:: With hydrazine hydrate; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ol4019562 DOI:10.1021/ol502316x

Reference yield:

: 1449117-92-3
(S)-4-benzyl-3-((S)-2-((S)-hydroxy(1-tosyl-1H-indol-3-yl)methyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

: 67215-36-5
iso-lysergic acid methyl ester

: 4579-64-0
lysergic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: hydrazine hydrate / tetrahydrofuran / 1 h / 0 °C

2.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / Inert atmosphere

3.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / Inert atmosphere

5.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 80 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver carbonate / toluene / 4 h / 100 °C / Inert atmosphere

8.1: methanol; magnesium / benzene / 1 h / 20 °C / Inert atmosphere

9.1: dmap / acetonitrile / 1 h / 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

11.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / Inert atmosphere

12.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C

13.1: diethyl ether; methanol / 0.25 h / 20 °C / Inert atmosphere

14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / Inert atmosphere

15.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / Inert atmosphere

15.2: 0.5 h / 50 °C / Inert atmosphere

16.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; methanol; triethylsilane; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; dimethylsulfide; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium cyanoborohydride; sodium hydrogencarbonate; hydrazine hydrate; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: |Heck Reaction;
DOI:10.1021/ol4019562