Water → (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate

HRID 1177534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177534
[F:1][C:2]1[CH:3]=[C:4]([C:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH:27]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.O>[Pd].C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:26]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C@H:28]([C:38]([O:40][CH3:41])=[O:39])[CH2:27]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:19][CH2:18]1)[N:11]=2

Komponenten

5

Edukt 2

HCID 962WaterHCID 67112968(2S)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2H-pyrrole-1,2(5H)-dicarboxylate

Produkt 1

HCID 67111920(2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(2S)-1-tert-Butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)-2H-pyrrole-1,2(5H)-dicarboxylate (0.618 g, 1.1 mmol) and 10% palladium on carbon, 50% water (0.58 g) were combined in a flask and treated with nitrogen and 10 mL THF. The reaction mixture was stirred rapidly under H2 balloon for 48 h. The reaction mixture was flushed with nitrogen, filtered, rinsing with DCM and concentrated in vacuo. Purification by silica gel chromatography, 40 g, 0-30% EA/hexanes gave (2S,4R)-1-tert-butyl 2-methyl 4-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)pyrrolidine-1,2-dicarboxylate as a yellow foam. MS (ESI) m/z: Calculated: 573.2; Observed: 573.7 (M++1).

Aufarbeitung

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered
  3. washrinsing with DCM
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography, 40 g, 0-30% EA/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6c31b1fdec9540ccaa6e10fd31f10d93
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

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