HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → L-Proline, N-(methoxycarbonyl)-L-valyl-4-hydroxy-, methyl ester, (4R)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4R)-4-Hydroxy-L-proline methyl ester | HCID 7015125 | — |
| 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 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | L-Proline, N-(methoxycarbonyl)-L-valyl-4-hydroxy-, methyl ester, (4R)- | HCID 58313116 | — |
Reaction Steps
To a solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester in dry DCM (200 mL) was added (S)-2-methoxycarbonylamino-3-methyl-butyric acid (10 g, 55 mmol), HATU (24 g, 63.25 mmol), and triethylamine (16.7 g, 165 mmol. The reaction mixture was stirred at RT overnight. DCM (200 mL) was added and the solution was washed with brine, dried, concentrated and purified by silica gel column chromatography (eluted with petroleum ether:EtOAc 10:1 to 1:4)) to give the title intermediate as a yellow oil (20 g). (m/z): [M+H]+ calcd for C13H22N2O6 303.15. found 303.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09212168B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-620faa5ba7d8450bb4339221b3c97eff |
| Source note | uspto-grants-2015_12 |