HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → (2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 4-Morpholineacetic acid | HCID 438968 | — |
| Reactant | Methyl L-threoninate hydrochloride | HCID 2734893 | — |
| 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 | (2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoate | HCID 117608206 | 48% |
Reaction Steps
HATU (7.66 g, 20.1 mmol) was added to a solution of 2-morpholinoacetic acid (2.44 g, 16.8 mmol) and (2S,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (2.84 g, 16.8 mmol) in dichloromethane (20 mL) at 0° C. N-Methylmorpholine (5.1 g, 50.4 mmol) was added and the reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. The mixture was concentrated and the residue was purified by flash column chromatography on silica gel (dichloromethane/methanol=100:1 to 60:1) to afford (2S,3R)-methyl 3-hydroxy-2-(2-morpholinoacetamido)butanoate (2.1 g, 48% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434761B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-1d62453ce0004896ace76155e6286cbf |
| Source note | uspto-grants-2016_09 |