Technology Process of (2S)-1-[(4S)-4-Benzyl-2-oxo-1,3-oxazolan-3-yl]-3-(4-tert-butoxycarbonyloxy-2,6-dimethylphenyl)-2-ethylpropan-1-one
There total 8 articles about (2S)-1-[(4S)-4-Benzyl-2-oxo-1,3-oxazolan-3-yl]-3-(4-tert-butoxycarbonyloxy-2,6-dimethylphenyl)-2-ethylpropan-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4S)-4-Benzyl-3-[3-(4-tert-butoxycarbonyloxy-2,6-dimethylphenyl)propanoyl]-1,3-oxazolan-2-one;
With
sodium hexamethyldisilazane;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
ethyl iodide;
In
tetrahydrofuran;
at -25 ℃;
for 3h;
DOI:10.1055/s-2001-16757
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 98 percent / Et3N; DMAP / H2O; tetrahydrofuran / 0.5 h / 20 °C
2.1: 61 percent / (o-MePh)3P; Et3N / Pd(OAc)2 / acetonitrile / 24 h / Heating
3.1: H2 / 10 percent Pd/C / ethyl acetate / 5 h / 60 °C / 3620.04 Torr
4.1: aq. NaOH / tetrahydrofuran / 20 °C
5.1: Et3N / diethyl ether / 1 h / 0 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C
6.2: 81 percent / tetrahydrofuran; diethyl ether; hexane / 0.75 h / -78 - 0 °C
7.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
7.2: 65 percent / tetrahydrofuran / 3 h / -25 °C
With
dmap; sodium hydroxide; n-butyllithium; hydrogen; sodium hexamethyldisilazane; triethylamine; tris-(o-tolyl)phosphine;
palladium diacetate; palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; hexane; water; ethyl acetate; acetonitrile;
2.1: Heck coupling;
DOI:10.1055/s-2001-16757
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 79 percent / KI; KIO3; HCl / methanol
2.1: 98 percent / Et3N; DMAP / H2O; tetrahydrofuran / 0.5 h / 20 °C
3.1: 61 percent / (o-MePh)3P; Et3N / Pd(OAc)2 / acetonitrile / 24 h / Heating
4.1: H2 / 10 percent Pd/C / ethyl acetate / 5 h / 60 °C / 3620.04 Torr
5.1: aq. NaOH / tetrahydrofuran / 20 °C
6.1: Et3N / diethyl ether / 1 h / 0 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C
7.2: 81 percent / tetrahydrofuran; diethyl ether; hexane / 0.75 h / -78 - 0 °C
8.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
8.2: 65 percent / tetrahydrofuran / 3 h / -25 °C
With
hydrogenchloride; dmap; potassium iodate; sodium hydroxide; n-butyllithium; hydrogen; sodium hexamethyldisilazane; triethylamine; tris-(o-tolyl)phosphine; potassium iodide;
palladium diacetate; palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; water; ethyl acetate; acetonitrile;
3.1: Heck coupling;
DOI:10.1055/s-2001-16757
