HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-2,7-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid | HCID 10942966 | — |
| Reactant | 2-(Tert-butyl) 7-ethyl 2,6-diazaspiro[3.4]octane-2,7-dicarboxylate | HCID 58313058 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-2,7-dicarboxylate | HCID 58313053 | 51.2% |
Reaction Steps
To a solution of 2-(1,1-dimethylethyl) 7-ethyl 2,6-diazaspiro[3.4]octane-2,7-dicarboxylate (145) (500 mg, 1.76 mmol), HATU (735 mg, 1.93 mmol) and N-[(methyloxy)carbonyl]-L-valine (339 mg, 1.93 mmol) in anhydrous CH2Cl2 (10 mL) was added Hunig's base (0.68 mL, 3.87 mmol) and the reaction stirred at room temperature under nitrogen for 2 h. The reaction was concentrated in vacuo and purified by C18 reverse-phase chromatography eluting with 10-90% ACN/water/0.2% NH4OH to afford the title compound as an off-white solid (398 mg, 51% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492554B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-83c90e1298e842c0bcb1664acd60a76e |
| Source note | uspto-grants-2013_07 |