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

HRID 910586노트

반응식

HRID 910586 반응식
[CH2:1]([C:8]1[C:9](=[O:20])[NH:10][N:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:12]=1[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:27]([O:33][C@@H:34]1[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[O:36][C@H:35]1Br)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[CH2:1]([C:8]1[C:9]([O:20][C@@H:35]2[O:36][C@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:50])([CH3:51])[CH3:52])[C@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@H:34]2[O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:29])[CH3:30])=[N:10][N:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:12]=1[CH:13]([CH3:14])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 53466083HCID 53466083, 화합물HCID 673490834-benzyl-1,2-dihydro-5-isopropyl-1-propionyl-3H-pyrazol-3-one

생성물 1

HCID 673487544-benzyl-5-isopropyl-1-propionyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole수율 84.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-benzyl-1,2-dihydro-5-isopropyl-1-propionyl-3H-pyrazol-3-one (1.25 g) in acetonitrile (25 mL) were added potassium carbonate (0.951 g) and 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl bromide (2.79 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 materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=20/1) to give 4-benzyl-5-isopropyl-1-propionyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (3.00 g).

후처리

  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 materials were 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=20/1)

출처 및 근거

ORD 기록
ord-37efa0c727604640bceb9bd43560edc9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022192B2

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