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 929254ノート

反応式

HRID 929254 の反応式
[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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  1. customThe reaction solution was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-7416ef8e1921435d8a3d3edd5a666fd3
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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