HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Bromo-4-fluorobenzoic acid → (2R,3R)-3-(3-bromo-4-fluoro-benzoylamino)-2-hydroxy-4-phenyl-butyric acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Bromo-4-fluorobenzoic acid | HCID 70509 | — |
| 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 | (2R,3R)-3-amino-2-hydroxy-4-phenyl-butyric acid ethyl ester | HCID 66864291 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R,3R)-3-(3-bromo-4-fluoro-benzoylamino)-2-hydroxy-4-phenyl-butyric acid ethyl ester | HCID 71073975 | — |
Reaction Steps
3-Bromo-4-fluorobenzoic acid (109 mg, 497 μmol, 1.0 eq.), DIPEA (273 μL, 3.2 eq.), HATU (189 mg, 497 μmol, 1.0 eq.), and (2R,3R)-3-amino-2-hydroxy-4-phenyl-butyric acid ethyl ester (129 mg, 497 μmol, 1.0 eq.) were combined in DCM (2 mL) and stirred for 1 hour. The crude reaction was then chromatographed (0-80% EtOAc/hexanes gradient) to yield (2R,3R)-3-(3-bromo-4-fluoro-benzoylamino)-2-hydroxy-4-phenyl-butyric acid ethyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08686184B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-f0ebe67e79f5497bb08afc99804b8134 |
| Source note | uspto-grants-2014_04 |