Technology Process of {(3R,4S)-1-[5-({1-[3-(1,1-difluoroethyl)[1,2,4]oxadiazol-5-yl]piperidin-4-yl}(2,2,2-trifluoroethyl)carbamoyl)pyrimidin-2-yl]-4-(2,5-difluorophenyl)pyrrolidin-3-yl}carbamic acid tert-butyl ester
There total 13 articles about {(3R,4S)-1-[5-({1-[3-(1,1-difluoroethyl)[1,2,4]oxadiazol-5-yl]piperidin-4-yl}(2,2,2-trifluoroethyl)carbamoyl)pyrimidin-2-yl]-4-(2,5-difluorophenyl)pyrrolidin-3-yl}carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
2-[(3R,4S)-3-tert-butoxycarbonylamino-4-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid;
With
pyridine; oxalyl dichloride;
In
dichloromethane; N,N-dimethyl-formamide;
for 1h;
Inert atmosphere;
{1-[3-(1,1-difluoroethyl)-[1,2,4]oxadiazol-5-yl]piperidin-4-yl}-(2,2,2-trifluoroethyl)amine;
With
pyridine;
In
dichloromethane;
at 20 ℃;
for 18h;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: sodium hydroxide / water; methanol / 0.67 h / 4 - 6 °C
1.2: Cooling with ice
2.1: dmap / 18 h / 0 - 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / dichloromethane / 1 h / -5 - 30 °C
4.1: hydrogen / RaNi / industrial methylated spritis / 18 h / 20 °C / 37503.8 Torr / Autoclave
5.1: di-tert-butyl dicarbonate / tetrahydrofuran / 18 h / 0 - 20 °C
6.1: isopropyl alcohol; diethyl ether; 2-Methylpentane / Resolution of racemate; Autoclave
7.1: hydrogen / palladium 10% on activated carbon / toluene; industrial methylated spirits / 78 h / 20 - 60 °C
8.1: triethylamine / 1,2-dichloro-ethane / 16 h / 20 °C
9.1: sodium hydroxide / water; tetrahydrofuran / 16 h / 20 °C
9.2: pH 6
10.1: oxalyl dichloride; pyridine / dichloromethane; N,N-dimethyl-formamide / 1 h / Inert atmosphere
10.2: 18 h / 20 °C
With
pyridine; dmap; oxalyl dichloride; di-tert-butyl dicarbonate; hydrogen; triethylamine; trifluoroacetic acid; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; industrial methylated spirits; diethyl ether; 2-Methylpentane; dichloromethane; industrial methylated spritis; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: dmap / 18 h / 0 - 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 1 h / -5 - 30 °C
3.1: hydrogen / RaNi / industrial methylated spritis / 18 h / 20 °C / 37503.8 Torr / Autoclave
4.1: di-tert-butyl dicarbonate / tetrahydrofuran / 18 h / 0 - 20 °C
5.1: isopropyl alcohol; diethyl ether; 2-Methylpentane / Resolution of racemate; Autoclave
6.1: hydrogen / palladium 10% on activated carbon / toluene; industrial methylated spirits / 78 h / 20 - 60 °C
7.1: triethylamine / 1,2-dichloro-ethane / 16 h / 20 °C
8.1: sodium hydroxide / water; tetrahydrofuran / 16 h / 20 °C
8.2: pH 6
9.1: oxalyl dichloride; pyridine / dichloromethane; N,N-dimethyl-formamide / 1 h / Inert atmosphere
9.2: 18 h / 20 °C
With
pyridine; dmap; oxalyl dichloride; di-tert-butyl dicarbonate; hydrogen; triethylamine; trifluoroacetic acid; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; industrial methylated spirits; diethyl ether; 2-Methylpentane; dichloromethane; industrial methylated spritis; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
![{1-[3-(1,1-difluoroethyl)-[1,2,4]oxadiazol-5-yl]piperidin-4-yl}-(2,2,2-trifluoroethyl)amine](/Databaselist/images/loading.webp)
