Hydrochloric Acid → HCID 86664426、化合物

HRID 46192ノート

反応式

HRID 46192 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH:47]([C:52]1[N:53]=[N:54][C:55]([Cl:58])=[CH:56][CH:57]=1)C(OC)=O.CO.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:58][C:55]1[N:54]=[N:53][C:52]([CH2:47][C:3]2[CH:4]=[C:5]([C@H:8]3[C@H:13]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C@@H:12]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:11]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[O:9]3)[CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:57][CH:56]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 86664427HCID 86664427、化合物2 回

生成物 1

HCID 86664426HCID 86664426、化合物収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Methyl 2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-2-(6-chloropyridazin-3-yl)acetate (compound 23, 9.9 g, 12 mmol) from Step 1 in terahydrofuran (40 mL) was added methanol (56 mL) and lithium hydroxide solution (0.1 M in water, 180 mL, 180 mmol). The reaction mixture was allowed to stir at room temperature overnight. After cooling to 0° C., hydrochloric acid (1.0 M) was added to neutralize the reaction mixture. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was slurried in methanol (100 mL) and the slurry was stirred at ambient temperature for 2 h. The resulting solid was isolated by filtration and dried in vacuo to yield the title compound (7.8 g, 10 mmol, 86%) as a white solid.

後処理

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringthe slurry was stirred at ambient temperature for 2 h
  8. customThe resulting solid was isolated by filtration
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-a809bb9576a44f1a8a4bb5645da53935
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

反応ノート

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