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1,8-Diazabicyclo(5.4.0)undec-7-ene → (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 1485604
ノート
印刷プレビュー

反応式

HRID 1485604 の反応式
[O:1]1[CH2:5][C@@H:4]([OH:6])[C@H:3]2[O:7][CH2:8][C@@H:9]([OH:10])[C@@H:2]12.N12CCCN=C1CCCCC2.[Cl:22][C:23]1[CH:24]=[C:25]2[N:32]=[C:31](S(C)(=O)=O)[N:30]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:26]2=[N:27][C:28]=1[I:29]>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]2[N:32]=[C:31]([O:6][C@H:4]3[C@H:3]4[O:7][CH2:8][C@@H:9]([OH:10])[C@H:2]4[O:1][CH2:5]3)[N:30]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:26]2=[N:27][C:28]=1[I:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109756241,4:3,6-Dianhydro-D-mannitolHCID 1235023166-Chloro-5-iodo-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine

生成物 1

HCID 123413447(3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

(3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diol (1.84 g) is dissolved in N,N-dimethylformamide (10 mL) and treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 1.9 mL). A solution of 6-chloro-5-iodo-2-(methylsulfonyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridine (2.05 g) in N,N-dimethylformamide (20 mL) is added drop wise and the mixture is stirred for 2 hours at room temperature. The mixture is partitioned between water and ethyl acetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→0:100) to give the title compound. LC (method 1): tR=1.17 min; Mass spectrum (ESI+): m/z=554 [M+H]+.

後処理

  1. customThe mixture is partitioned between water and ethyl acetate
  2. washthe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvents are evaporated in vacuo
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→0:100)

出典と根拠

ORDレコード
ord-d770946225894cee90db59537512ef90
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422312B2

反応ノート

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