Potassium Carbonate → 1-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole

HRID 910584ノート

反応式

HRID 910584 の反応式
[C:1]([N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6](=[O:19])[NH:5]1)(=[O:3])[CH3:2].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]>C(#N)C>[C:1]([N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:6]([O:19][C@@H:34]2[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]2[O:32][C:26](=[O:31])[C:27]([CH3:30])([CH3:28])[CH3:29])=[N:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 53466083HCID 53466083、化合物HCID 67348858HCID 67348858、化合物

生成物 1

HCID 116147111-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole収率 72.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 1-acetyl-4-benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (1.26 g) in acetonitrile (20 mL) were added potassium carbonate (1.01 g) and 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl bromide (2.96 g) under stirring at room temperature. In addition, the mixture was heated to 50° C. and stirred for 3 hours. After the completion of the reaction, the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 1-acetyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (2.68 g).

後処理

  1. temperatureIn addition, the mixture was heated to 50° C.
  2. stirringstirred for 3 hours
  3. customAfter the completion of the reaction
  4. customthe insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-e1d43988dbf3454290464e403d634449
出典データセット
uspto-grants-2011_09
特許番号
US08022192B2

反応ノート

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