Water → HCID 67341046、化合物

HRID 2223949ノート

反応式

HRID 2223949 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([OH:19])[C:11]=23)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:26]([O:32][C@@H:33]1[C@@H:38]([O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[C@H:37]([O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:36]([CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[O:35][C@@H:34]1Br)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[NH:16][N:17]=[C:18]([O:19][C@@H:34]4[O:35][C@H:36]([CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[C@@H:37]([O:46][C:47](=[O:52])[C:48]([CH3:49])([CH3:50])[CH3:51])[C@H:38]([O:39][C:40](=[O:45])[C:41]([CH3:42])([CH3:43])[CH3:44])[C@H:33]4[O:32][C:26](=[O:31])[C:27]([CH3:30])([CH3:28])[CH3:29])[C:11]=23)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10886360((2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl)methyl 2,2-dimethylpropanoateHCID 1785159974-[2-(4-Hydroxyphenyl)ethyl]-1H-pyrazolo[3,4-b]-pyridin-3-ol

生成物 1

HCID 67341046HCID 67341046、化合物収率 22%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-[2-(4-Hydroxyphenyl)ethyl]-1H-pyrazolo[3,4-b]-pyridin-3-ol (3.48 g) was stirred at 100° C. to be dissolved in N,N-dimethylformamide (55 mL). The solution was cooled to room temperature. To the solution were added potassium carbonate (3.77 g) and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (9.48 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2-1/1-2/3) to give the title compound (2.26 g).

後処理

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/2-1/1-2/3)

出典と根拠

ORDレコード
ord-5259e973ca684606967f34f59091f523
出典データセット
uspto-grants-2008_05
特許番号
US07375113B2

反応ノート

読み込み中…