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

HRID 7395

반응식

HRID 7395 반응식
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=3)=[C:16]([CH3:29])[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+].[CH:36]1(Br)[CH2:40][CH2:39][CH2:38][CH2:37]1.O>CN(C)C=O>[CH:36]1([N:15]2[C:16]([CH3:29])=[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:27])[CH3:28])=[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)[CH2:40][CH2:39][CH2:38][CH2:37]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 10796Cesium carbonateHCID 98015583-(beta-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole

생성물 1

HCID 691343861-cyclopentyl-3-(beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole수율 58.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) and cesium carbonate (0.20 g) in N,N-dimethylformamide (1 mL) was added cyclopentyl bromide (0.055 g) at 80° C., and the mixture was stirred for 30 minutes. After cooling to room temperature, water was added to the reaction mixture, 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=8/1) to give 1-cyclopentyl-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.034 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-c3d1338347874e4b9770a415431dc81b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087579B2

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