HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → 3-(2-Benzyloxy-propionylamino)-3H-imidazole-4-carboxylic acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 2-(Benzyloxy)propanoic acid | HCID 245987 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 3-(2-Benzyloxy-acetylamino)-3H-imidazole-4-carboxylic acid methyl ester | HCID 89715196 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 3-(2-Benzyloxy-propionylamino)-3H-imidazole-4-carboxylic acid methyl ester | HCID 89715195 | 91% |
Reaktionsschritte
To a solution of compound 2 (4.2 g, 29.7 mmol), 2-Benzyloxy-propionic acid (5.5 g, 29.7 mmol) and DIEA (10 mL) in a mixture of DMF (1 mL) and THF (50 mL) in ice-water bath was added HATU (13.5 g, 35.7 mmol). The resulting mixture was then stirred at ambient temperature overnight. Water (100 mL) was added. The mixture was extracted with ethyl acetate (300 mL×2). The combined organic phases were concentrated to give a crude residue, which was purified by chromatography on silica gel column (eluted with PE/EtOAc=1:1 to 1:3) to afford compound 9 (8.2 g, 91% yield) as brown oil. LC-MS: m/z 304 [M+H]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09434733B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-efc87d032fbe4100bf345dd07e40e300 |
| Quellennotiz | uspto-grants-2016_09 |