HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → Tert-butyl-2,2-difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| 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 | 2-(Propan-2-yl)-1,3-thiazole-4-carboxylic acid | HCID 22573065 | — |
| Edukt | tert-Butyl 2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate | HCID 57989014 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | Tert-butyl-2,2-difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate | HCID 57989035 | — |
Reaktionsschritte
HATU (1.184 g) was added to a solution of tert-butyl 2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 37, step c) (0.7 g) and 2-isopropylthiazole-4-carboxylic acid (0.41 g) and triethylamine (1 mL) in DMF (12 mL) at 20° C. and the resultant mixture stirred for 1 hour. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.78 g.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08629271B2 |
| Quelldatensatz | uspto-grants-2014_01 |
| ORD ID | ord-636025a4cdf747678a0de17a05c6da7a |
| Quellennotiz | uspto-grants-2014_01 |