Tetrahydrofuran → HCID 86621495, Verbindung

HRID 61503

Reaktionsgleichung

Reaktionsgleichung von HRID 61503
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[CH2:11][CH2:12][N:13]([C:16]([C@@H:18]3[C@@H:23]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][C@@H:21]([OH:28])[CH2:20][N:19]3[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:17])[CH2:14][CH:15]=2)=[CH:5][C:4]=1[CH3:36])#[N:2].O1CCCC1.[Cl:42][C:43]1[CH:44]=[C:45](O)[CH:46]=[N:47][CH:48]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[Cl:42][C:43]1[CH:44]=[C:45]([O:28][C@@H:21]2[CH2:20][N:19]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C@H:18]([C:16]([N:13]3[CH2:12][CH:11]=[C:10]([C:6]4[CH:7]=[C:8]([CH3:9])[C:3]([C:1]#[N:2])=[C:4]([CH3:36])[CH:5]=4)[CH2:15][CH2:14]3)=[O:17])[C@@H:23]([C:24]([O:26][CH3:27])=[O:25])[CH2:22]2)[CH:46]=[N:47][CH:48]=1

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5823053-Hydroxy-5-chloropyridineHCID 86621496HCID 86621496, Verbindung

Produkt 1

HCID 86621495HCID 86621495, VerbindungAusbeute 36,9 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 3-methyl(2S,3S,5R)-2-[4-(4-cyano-3,5-dimethylphenyl)-3,6-dihydropyridin-1(2H)-yl]carbonyl-5-hydroxypiperidine-1,3-dicarboxylate (100 mg, 0.0002 mol) in tetrahydrofuran (0.912 mL, 0.0112 mol) was added 5-chloropyridin-3-ol (35.0 mg, 0.000270 mol), triphenylphosphine (70.8 mg, 0.000270 mol), followed by diisopropyl azodicarboxylate (0.0532 mL, 0.000270 mol). The mixture was heated at 70 Celsius overnight. After concentrated to dry, the mixture was purified on silica gel, elution with 0 to 40% EtOAc in hexane, to yield the desired product (45 mg, 32.84%). MS (ESI) (M+H) 609.1.

Aufarbeitung

  1. concentrationAfter concentrated
  2. customto dry
  3. customthe mixture was purified on silica gel, elution with 0 to 40% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4c4af428e94848f48b61608bf4d97099
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

Verknüpfte Notizen

Wird geladen…