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Water → 4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3-(6-O-propionyl-beta-D-glucopyranosyloxy)pyrazole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | 2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) | HCID 22230 | — |
| 反応物 | Propionyl chloride | HCID 62324 | — |
| 反応物 | Remogliflozin | HCID 9846588 | — |
| 溶媒 | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| 生成物 | 4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3-(6-O-propionyl-beta-D-glucopyranosyloxy)pyrazole | HCID 67335748 | 65.8% |
反応手順
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 propionyl chloride (0.072 g) at 0° C., and the mixture was stirred for 5 hours. 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=10/1) afforded 4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3-(6-O-propionyl-β-D-glucopyranosyloxy)pyrazole (0.074 g)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07084123B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-9fb0be25a7f347229a8718714c82051f |
| 出典メモ | uspto-grants-2006_08 |