Technology Process of (S)-1-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-piperazine-2-carboxylic acid tert-butylamide
There total 22 articles about (S)-1-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-piperazine-2-carboxylic acid tert-butylamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
cyclohexa-1,4-diene; hydrogen;
palladium on activated charcoal;
In
ethyl acetate;
at 23 ℃;
for 1.3h;
under 760.051 Torr;
DOI:10.1021/ja010113y
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C
2.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C
3.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C
4.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C
5.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C
5.2: sodium tetraborate; KMnO4 / 2-methyl-propan-2-ol; H2O / 0.25 h / 0 °C
5.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH2Cl2
6.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C
7.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C
8.1: 85 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C
9.1: 78 percent / propan-2-ol / 13 h / 80 °C
10.1: 90 percent / 1,4-cyclohexadiene; H2 / Pd/C / ethyl acetate / 1.3 h / 23 °C / 760.05 Torr
With
lithium borohydride; methanesulfonic acid; cyclohexa-1,4-diene; potassium tert-butylate; hydrogen bromide; hydrogen; toluene-4-sulfonic acid; acetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; ethyl acetate; isopropyl alcohol; tert-butyl alcohol;
DOI:10.1021/ja010113y
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: (COCl)2; DMF / CH2Cl2 / 0 - 23 °C
2.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C
3.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C
4.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C
5.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C
6.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C
6.2: sodium tetraborate; KMnO4 / 2-methyl-propan-2-ol; H2O / 0.25 h / 0 °C
6.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH2Cl2
7.1: 88 percent / p-toluenesulfonic acid monohydrate / methanol / 3 h / 23 °C
8.1: 89 percent / methanesulfonic acid / ethyl acetate / 3 h / 23 °C
9.1: 85 percent / t-BuOK / tetrahydrofuran / 0.25 h / 0 °C
10.1: 78 percent / propan-2-ol / 13 h / 80 °C
11.1: 90 percent / 1,4-cyclohexadiene; H2 / Pd/C / ethyl acetate / 1.3 h / 23 °C / 760.05 Torr
With
lithium borohydride; oxalyl dichloride; methanesulfonic acid; cyclohexa-1,4-diene; potassium tert-butylate; hydrogen bromide; hydrogen; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; isopropyl alcohol; tert-butyl alcohol;
DOI:10.1021/ja010113y
![(S)-4-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester](/Databaselist/images/loading.webp)
