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Sodium Hydroxide → 3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-bromophenyl)methyl]-5-isopropyl-1H-pyrazole

HRID 1442368
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HRID 1442368 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:17])[NH:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH3:18][C:19]([O:21][CH2:22][C@H:23]1[O:28][C@H:27](Br)[C@H:26]([O:30][C:31]([CH3:33])=[O:32])[C@@H:25]([O:34][C:35]([CH3:37])=[O:36])[C@@H:24]1[O:38][C:39]([CH3:41])=[O:40])=[O:20].[OH-].[Na+]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[C:31]([O:30][C@@H:26]1[C@@H:25]([O:34][C:35](=[O:36])[CH3:37])[C@H:24]([O:38][C:39](=[O:40])[CH3:41])[C@@H:23]([CH2:22][O:21][C:19](=[O:20])[CH3:18])[O:28][C@H:27]1[O:17][C:10]1[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[C:13]([CH:14]([CH3:15])[CH3:16])[NH:12][N:11]=1)(=[O:32])[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 589519854-[(4-Bromophenyl)methyl]-1,2-dihydro-5-isopropyl-3h-pyrazol-3-one

생성물 1

HCID 685357693-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-bromophenyl)methyl]-5-isopropyl-1H-pyrazole수율 38.9%

시약·촉매·용매 2

HCID 159952
Benzyltributylammonium chloride
촉매
HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4-[(4-bromophenyl)methyl]-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (5.0 g) in dichloro-methane (50 mL) were added acetobromo-α-D-glucose (7.0 g), benzyltri(n-butyl)ammonium chloride (5.3 g) and 5 mol/L aqueous sodium hydroxide solution (8.5 mL), and the mixture was stirred at room temperature overnight. The organic layer was separated, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give the title compound (4.12 g).

후처리

  1. customThe organic layer was separated
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-bfcb1d7ec46b41a3b5b65e21e530a503
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07655632B2

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