(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

Base Information

Chemical Name:(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester
CAS No.:792948-37-9
Molecular Formula:C₂₅H₂₄N₂O₅
Molecular Weight:432.476
Hs Code.:

Synonyms:(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

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Chemical Property of (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

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Technology Process of (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

There total 7 articles about (11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester 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%

: 140-88-5,9003-32-1
ethyl acrylate

: 792948-35-7
(S)-9-benzyloxy-8-methyl-2-vinyl-3,11a-dihydro-10H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11-dione

: 792948-37-9
(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

Guidance literature:: With [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxy-3-Ph-C₆H₃); In dichloromethane; at 20 ℃; for 17h;
DOI:10.1016/j.tet.2004.07.040

Reference yield:

: 792948-36-8
(S)-4-methylsulfanyl-2-prop-2-ynylaminobutyric acid methyl ester

: 792948-37-9
(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / aq. KHCO₃ / ethyl acetate / 14 h / 0 °C

2: 100 percent / aq. NaIO₄ / methanol / 4 h / 0 °C

3: 37 percent / xylene / 60 h / 140 °C

4: 76 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / 20 °C

5: TMSCl; NaI / acetonitrile / 10 h / 20 °C

6: 93 mg / Et₃N / CH₂Cl₂ / 12 h / 0 °C

7: Zn; AcOH / CH₂Cl₂ / 0.33 h / 20 °C

8: 451 mg / aq. HCl / tetrahydrofuran / 24 h / 20 °C

9: 60 percent / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxy-3-Ph-C₆H₃) / CH₂Cl₂ / 17 h / 20 °C

With hydrogenchloride; sodium periodate; Grubbs catalyst first generation; chloro-trimethyl-silane; [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxy-3-Ph-C₆H₃); potassium hydrogencarbonate; acetic acid; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile; xylene;
DOI:10.1016/j.tet.2004.07.040

Reference yield:

: 792948-18-6
(S)-methyl 2-(((benzyloxy)carbonyl)(prop-2-yn-1-yl)amino)-4-(methylthio)butanoate

: 792948-37-9
(11aS)-3-(9-benzyloxy-8-methyl-5,11-dioxo-5,10,11,11a-tetrahydro-3H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / aq. NaIO₄ / methanol / 4 h / 0 °C

2: 37 percent / xylene / 60 h / 140 °C

3: 76 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / 20 °C

4: TMSCl; NaI / acetonitrile / 10 h / 20 °C

5: 93 mg / Et₃N / CH₂Cl₂ / 12 h / 0 °C

6: Zn; AcOH / CH₂Cl₂ / 0.33 h / 20 °C

7: 451 mg / aq. HCl / tetrahydrofuran / 24 h / 20 °C

8: 60 percent / [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxy-3-Ph-C₆H₃) / CH₂Cl₂ / 17 h / 20 °C

With hydrogenchloride; sodium periodate; Grubbs catalyst first generation; chloro-trimethyl-silane; [1,3-Mes₂-(N₂C₃H₅)]Cl₂Ru=CH(2-isopropoxy-3-Ph-C₆H₃); acetic acid; triethylamine; sodium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; xylene;
DOI:10.1016/j.tet.2004.07.040