HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 1-(cyclopropylmethyl)-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Ethyl chloroformate | HCID 10928 | — |
| Edukt | 2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) | HCID 22230 | — |
| Edukt | 1-(cyclopropylmethyl)-3-(beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole | HCID 69133847 | — |
| Lösungsmittel | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| Produkt | 1-(cyclopropylmethyl)-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole | HCID 23545513 | 74,4% |
Reaktionsschritte
To a solution of 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) in 2,4,6-trimethylpyridine (1 mL) was added ethyl chloroformate (0.035 g), and the mixture was stirred at room temperature overnight. Citric acid monohydrate (3.3 g) and water were 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=10/1) to give 1-(cyclopropylmethyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.043 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07189702B2 |
| Quelldatensatz | uspto-grants-2007_03 |
| ORD ID | ord-db6b39c663a94570a5b34dcc5ba6ff75 |
| Quellennotiz | uspto-grants-2007_03 |