Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| 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)-N-Boc-amino-non-8-enoic acid | HCID 11507316 | — |
| Reactant | (S)-tert-butyl 2-(((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidine-1-carboxylate | HCID 67106621 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86611239 | HCID 86611239 | 92.6% |
Reaction Steps
The dipeptide 1b from Step A (1.19 g, 3.38 mmol) was dissolved in HCl in dioxane (4.0 M, 13 mL, 51 mmol) and stirred at rt for 90 min to remove the Boc protective group. It was then concentrated down, taken up in acetonitrile and concentrated down again twice. This light brownish residue, 2(S)-tert-butoxycarbonylamino-non-8-enoic acid (0.95 g, 3.3 mmol) and HATU (1.4 g, 3.6 mmol) were dissolved in acetonitrile and cooled to 0° C. DIEA in acetonitrile was added drop-wise. The resulted mixture was allowed to warm to room temperature and stirred at room temperature for 10 h. The resulted mixture was concentrated, mixed with EtOAc, washed with aqueous saturated sodium bicarbonate, dried with Na2SO4, and concentrated. The residue was purified by silica gel chromatography (10% EtOAc and then 30% EtOAc) to give product 1d as pale yellowish oil (1.5 g, 90%). MS (ESI+): 528 [M+23] (5) and 406 [M+1−100] (100).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07829665B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-cb2b2cedfdd3499d8976f1da0fe83a8d |
|---|
| Source note | uspto-grants-2010_11 |
|---|
