Trifluoroacetic acid → (3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 929256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929256
[Cl:1][C:2]1[CH:3]=[C:4]2[N:16](COCC[Si](C)(C)C)[C:15]([O:25][C@H:26]3[C@H:30]4[O:31][CH2:32][C@@H:33]([OH:34])[C@H:29]4[O:28][CH2:27]3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH2:9][CH2:10][S:11][CH2:12][CH:13]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:16][C:15]([O:25][C@H:26]3[C@H:30]4[O:31][CH2:32][C@@H:33]([OH:34])[C@H:29]4[O:28][CH2:27]3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH2:13][CH2:12][S:11][CH2:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90041813(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Produkt 1

HCID 90067601(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To (3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (74 mg, 0.141 mmol) in anhydrous DCM (0.45 mL) was added TFA (0.45 mL, 5.84 mmol). The solution stirred at RT for 18 h. The reaction solution was added to saturated NaHCO3 (35 mL) and extracted with EtOAc (2×45 mL). The organic layers combined, dried over Na2SO4, filtered, and the filtrate evaporated under reduced pressure. Flash chromatography utilizing a 12 g silica RediSep Rf® Gold column and employing a 0-10% MeOH/DCM gradient afforded the title compound. LC-MS: calculated for C17H18ClN3O4S 395.07 observed m/e: 395.90 (M+H)+ (Rt 0.84/2.0 min)

Aufarbeitung

  1. extractionextracted with EtOAc (2×45 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-efe0960a906e4587a421f73ff82db798
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290517B2

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