Water → tert-butyl (3S,5R)-3-{[(5,6-difluoro-1H-benzimidazol-2-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 1259926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1259926
[F:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:16][CH:17]([CH3:41])[CH2:18][NH:19][C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH2:23][N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:21]1.C(=O)([O-])[OH:43].[Na+].O>C1COCC1>[F:1][C:2]1[C:14]([F:15])=[CH:13][C:5]2[NH:6][C:7]([C:9]([N:19]([CH2:18][CH:17]([CH3:41])[CH3:16])[C@H:20]3[CH2:25][C@@H:24]([C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])[CH2:23][N:22]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:21]3)=[O:43])=[N:8][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 231319195,6-difluoro-2-(trichloromethyl)-1H-benzimidazoleHCID 59356577tert-Butyl (3S,5R)-3-(isobutylamino)-5-(morpholine-4-carbonyl)piperidine-1-carboxylate

Produkt 1

HCID 58355165tert-butyl (3S,5R)-3-{[(5,6-difluoro-1H-benzimidazol-2-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5,6-difluoro-2-(trichloromethyl)-1H-benzimidazole (500 mg) and tert-butyl (3S,5R)-3-[(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (680 mg) in THF (50 ml) were added sodium hydrogen carbonate (1.3 g) and water (20 ml), and the mixture was stirred at room temperature for 1 hr and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) was concentrated under reduced pressure to give the object product (710 mg).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b52d8dc64cc345bd8f3dd83c91ac8a9c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466282B2

Notizen zur Reaktion

Wird geladen…