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

HRID 929254노트

반응식

HRID 929254 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[N:15](COCC[Si](C)(C)C)[C:14]([O:24][C@H:25]3[C@H:29]4[O:30][CH2:31][C@@H:32]([OH:33])[C@H:28]4[O:27][CH2:26]3)=[N:13][C:5]2=[N:6][C:7]=1[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:15][C:14]([O:24][C@H:25]3[C@H:29]4[O:30][CH2:31][C@@H:32]([OH:33])[C@H:28]4[O:27][CH2:26]3)=[N:13][C:5]2=[N:6][C:7]=1[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 90042471(3R,3aR,6R,6aR)-6-((6-chloro-5-(cyclopent-1-en-1-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 90067193(3R,3aR,6R,6aR)-6-((6-chloro-5-(cyclopent-1-en-1-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-(cyclopent-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (15 mg, 0.030 mmol) in anhydrous DCM (0.55 mL) was added TFA (0.55 mL, 7.13 mmol). The solution stirred at RT for 54 h. The reaction solution was evaporated under reduced pressure. Flash chromatography utilizing a 4 g silica RediSep Rf® Gold column and employing a 0-20% (1% NH4OH in MeOH)/DCM gradient afforded the title compound. LC-MS: calculated for C17H18ClN3O4 363.10 observed m/e: 364.11 (M+H)+ (Rt 1.20/2.0 min).

후처리

  1. customThe reaction solution was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-7416ef8e1921435d8a3d3edd5a666fd3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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