Water → Remogliflozin Etabonate

HRID 6658

反応式

HRID 6658 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 9846588Remogliflozin

生成物 1

HCID 9871420Remogliflozin Etabonate収率 72.4%

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b17bdad534cf48f2a7bb48b047be9ec0
出典データセット
uspto-grants-2006_08
特許番号
US07084123B2

関連ノート

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