Cesium carbonate → (4'-(6-chloro-2-(((3R,5 S,6R)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-yl)((R)-3-hydroxypyrrolidin-1-yl)methanone

HRID 1050262ノート

反応式

HRID 1050262 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[N:38](COCC[Si](C)(C)C)[C:37](S(C)(=O)=O)=[N:36][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:26][CH2:25][C@@H:24]([O:27]COCC[Si](C)(C)C)[CH2:23]3)=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.C1(C2[O:62][C@H:61]3[CH2:63][C@@H:64]([OH:67])[CH2:65][O:66][C@@H:60]3[CH2:59][O:58]2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:38][C:37]([O:67][C@@H:64]3[CH2:63][C@H:61]([OH:62])[C@@H:60]([CH2:59][OH:58])[O:66][CH2:65]3)=[N:36][C:5]2=[N:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[O:21])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 217656031,5-Anhydro-4,6-O-benzylidene-3-deoxy-D-glucitolHCID 90060767[4-[4-[6-chloro-2-methylsulfonyl-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]phenyl]-[(3R)-3-(2-trimethylsilylethoxymethoxy)pyrrolidin-1-yl]methanone

生成物 1

HCID 73332561(4'-(6-chloro-2-(((3R,5 S,6R)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-yl)((R)-3-hydroxypyrrolidin-1-yl)methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (R)-(4′-(6-chloro-2-(methylsulfonyl)-1-((2 (trimethylsilyl)ethoxy)-methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1′-biphenyl]-4-yl)(3-((2-(trimethylsilyl)-ethoxy)methoxy)pyrrolidin-1-yl)methanone (150 mg, 0.198 mmol) and (4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (100 mg, 0.423 mmol) in DMF (2 mL), was added cesium carbonate (150 mg, 0.460 mmol). The reaction mixture was stirred at room temperature for 2 h, then partitioned between water and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The chromatography of the resulting residue over silica (preparative TLC) eluting with 25% EtOAc in Hexanes afforded the title compound (Rf:0.7) LC-MS: calculated for C48H61ClN4O8Si2 912.37, observed m/e: 913.6 (M+H)+ (Rt: 3.30/4 min)

後処理

  1. custompartitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe chromatography of the resulting residue over silica (preparative TLC) eluting with 25% EtOAc in Hexanes

出典と根拠

ORDレコード
ord-7a9cf4f6c94b48098202a4a15d32fdb6
出典データセット
uspto-grants-2016_07
特許番号
US09382243B2

反応ノート

読み込み中…