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 929256ノート

反応式

HRID 929256 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-efe0960a906e4587a421f73ff82db798
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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