Sodium Hydroxide → 5-((3aR,6aS)-5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinic Acid

HRID 240504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240504
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([N:12]2[CH2:16][C@@H:15]3[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][C@@H:14]3[CH2:13]2)[CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O.C(OCC)(=O)C>[C:23]([O:22][C:20]([N:18]1[CH2:19][C@H:14]2[CH2:13][N:12]([C:8]3[CH:9]=[N:10][CH:11]=[C:6]([CH:7]=3)[C:4]([OH:5])=[O:3])[CH2:16][C@H:15]2[CH2:17]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 67265661(3aR,6aS)-tert-butyl 5-(5-(ethoxycarbonyl)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Produkt 1

HCID 672653675-((3aR,6aS)-5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)nicotinic AcidAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from Example 33A (3.20 g, 8.90 mmol) was dissolved in a solvent mixture of ethanol (40 mL) and water (20 mL). Sodium hydroxide (2.0 M, 13 mL) was added, and the reaction mixture was stirred at ambient temperature for 1 hour. The mixture was then diluted with ethyl acetate (100 mL) and partitioned between ethyl acetate (250 mL) and water (30 mL). The aqueous layer was acidified to pH 4 and repartitioned between dichloromethane (200 mL) and water (250 mL). The organic layer was dried (Na2SO4) and concentrated under vacuum to afford the title compound (3.0 g, 102%). 1H NMR (400 MHz, CD3OD) δ ppm 1.45 (s, 9H), 3.06-3.14 (br s, 2H), 3.27-3.34 (m, 4H), 3.61 (dd, J=10.0, 7.5 Hz, 2H), 3.64-3.71 (m, 2H), 7.57 (dd, J=2.8, 1.8 Hz, 1H), 8.04 (d, J=1.5 Hz, 1H), 8.39 (s, 1H). MS (APCI) m/z 334 (M+H)+.

Aufarbeitung

  1. custompartitioned between ethyl acetate (250 mL) and water (30 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e750d2d2029c4ecb89b208ae42f22524
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648084B2

Notizen zur Reaktion

Wird geladen…