HRID6658

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID10928

Ethyl chloroformate

C3H5ClO2

HCID22230

1,2,3-Propanetricarboxylic acid, 2-hydroxy-, hydrate (1:1)

C6H10O8

结构：Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C

HCID9846588

Remogliflozin

C23H34N2O7

PRODUCTS

生成物

结构：CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O

HCID9871420

5-Methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1H-pyrazol-3-yl 6-O-(ethoxycarbonyl)-beta-D-glucopyranoside

C26H38N2O9

收率 72.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID7953

2,4,6-Trimethylpyridine

C8H11N

PROCEDURE

实验过程

To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole (0.10 g) in 2,4,6-trimethylpyridine (1 mL) was added ethyl chloroformate (0.072 g), and the mixture was stirred at room temperature overnight. To the reaction mixture were added citric acid monohydrate (3.3 g) and water, and the resulting mixture was purified by ODS solid phase extraction (washing solvent: distilled water, eluent: methanol). Further purification by column chromatography on silica gel (eluent: dichloromethane/methanol=1011) and recrystalization (recrystalization solvent: ethyl acetate/hexane=1/3) afforded 3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole (0.084 g).

WORKUP

后处理

distillationthe resulting mixture was purified by ODS solid phase extraction (washing solvent: distilled water, eluent: methanol)
customFurther purification by column chromatography
customon silica gel (eluent: dichloromethane/methanol=1011) and recrystalization (recrystalization solvent: ethyl acetate/hexane=1/3)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b17bdad534cf48f2a7bb48b047be9ec0
来源数据集: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07084123B2
来源说明: uspto-grants-2006_08

反应 SMILES

[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])[N:15]([CH:30]([CH3:32])[CH3:31])[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].Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CC1C=C(C)C=C(C)N=1>[CH2:37]([O:36][C:34]([O:11][CH2:10][C@H:8]1[O:9][C@@H:1]([O:12][C:13]2[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:16]([CH3:29])[N:15]([CH:30]([CH3:32])[CH3:31])[N:14]=2)[C@H:2]([OH:3])[C@@H:4]([OH:5])[C@@H:6]1[OH:7])=[O:35])[CH3:38]