HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → Tert-butyl 3-(5-bromopicolinamido)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromopyridine-2-carboxylic acid | HCID 608544 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Product | Tert-butyl 3-(5-bromopicolinamido)propanoate | HCID 71060050 | — |
Reaction Steps
Solid HATU (4.0 g, 10.6 mmol) was added to a THF solution (100 mL) of 5-bromopicolinic acid (2.1 g, 10.6 mmol), i-Pr2NEt (7.4 mL, 42.4 mmol), and (3-alanine t-butyl ester hydrochloride (2.1 g, 11.7) and the resulting mixture was warmed to 45° C. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748624B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-6f2bc008926d4aaab76bc05bcbc7de95 |
| Source note | uspto-grants-2014_06 |