Water → 3-(beta-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole

HRID 457519

반응식

HRID 457519 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][CH2:36][CH2:37][OH:38].O>CN(C)C=O>[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])[N:15]([CH2:35][CH2:36][CH2:37][OH:38])[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 99526103-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole

생성물 1

HCID 235455153-(beta-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
40 °C

실험 절차

To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.020 g) and cesium carbonate (0.11 g) in N,N-dimethylformamide (0.5 mL) was added 3-bromopropanol (0.022 mL), and the mixture was stirred at 40° C. overnight. To the reaction mixture was added water, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol), and successively by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1) to give 3-(β-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.011 g).

후처리

  1. distillationthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

출처 및 근거

ORD 기록
ord-3296f2528543446f9322fed144ae8708
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189702B2

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