Water → tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 1260114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260114
Cl[C:2](Cl)(Cl)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.[N:14]1([C:20]([C@@H:22]2[CH2:27][C@H:26]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:25][N:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:23]2)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[OH2:39]>C1COCC1.C(=O)(O)[O-].[Na+]>[NH:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[C:2]([N:28]([CH2:29][CH2:30][CH3:31])[C@H:26]1[CH2:27][C@@H:22]([C:20]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:21])[CH2:23][N:24]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:25]1)=[O:39]

Komponenten

6

Edukt 3

HCID 962WaterHCID 77133Benzimidazole, 2-trichloromethyl-HCID 58355640tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate

Produkt 1

HCID 58355218tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

2-(Trichloromethyl)-1H-benzimidazole (1.09 g) and tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate (1.49 g) were dissolved in THF (120 ml), sodium hydrogen carbonate (3.52 g) and water (60 ml) were added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (2:8-10:0) was concentrated under reduced pressure to give the object product (1.97 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (2:8-10:0)
  6. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1af8277b28f8452eae9a921793f3e997
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466282B2

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