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 929256노트

반응식

HRID 929256 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-efe0960a906e4587a421f73ff82db798
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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