Sodium Iodide → 1-(cyclopropylmethyl)-3-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole

HRID 457521

반응식

HRID 457521 반응식
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)=[C:16]([CH3:27])[NH:15][N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][CH:36]1[CH2:38][CH2:37]1.[I-].[Na+]>CN(C)C=O.O>[CH:36]1([CH2:35][N:15]2[C:16]([CH3:27])=[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[C:13]([O:12][C@@H:1]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]3[OH:3])=[N:14]2)[CH2:38][CH2:37]1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 99526103-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole

생성물 1

HCID 235455141-(cyclopropylmethyl)-3-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.081 g) in N,N-dimethylformamide (1 mL) were added cesium carbonate (0.40 g), bromomethylcyclopropane (0.099 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 7 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1) to give 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.041 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1)

출처 및 근거

ORD 기록
ord-40523d8aeb5c4977bc68c1d0bd3362d3
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189702B2

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