Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | (S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid | HCID 2755934 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58293420 | HCID 58293420 | 99.1% |
Reaction Steps
To a mixture of (S)-2-(tert-butoxycarbonylamino)butanoic acid (1.4 g, 6.89 mmol), HATU (3.14 g, 8.27 mmol), and pyrrolidine (1.216 mL, 13.78 mmol) in DCM (50 mL) was added Et3N (1.920 mL, 13.78 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound as a light yellow oil (1.75 g, 99%). 1H NMR (500 MHz, CDCl3) δ 0.94 (t, J=7.57 Hz, 3 H) 1.34-1.48 (m, 9 H),1.49-1.68 (m, 1 H) 1.68-1.81 (m, 1 H) 1.81-1.92 (m, 2 H) 1.92-2.03 (m, 2 H) 3.34-3.47 (m,2 H) 3.52 (dt, J=12.08, 7.14 Hz, 1 H) 3.65 (dt, J=10.13, 6.65 Hz, 1 H) 4.30-4.42 (m, 1 H) 5.35 (d, J=8.30 Hz, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08420816B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-ad5030b539774bc48b567a069d341e7b |
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| Source note | uspto-grants-2013_04 |
|---|
