HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester | HCID 67969425 | — |
| Reactant | HCID 178524642 | HCID 178524642 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester | HCID 67969400 | 98% |
Reaction Steps
(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester (100 mg, 0.3 mmol, 1.0 eq.) and 3-hydroxyisoxazole-5-carboxylic acid (50.5 mg, 391 μmol, 1.5 eq.) were combined in DMF (5 mL) and the resulting mixture was stirred for 2 minutes. DIPEA was added and the resulting mixture was stirred for 1 hour. The material was dried under vacuum then purified using reverse phase chromatography to yield the title compound (40 mg, 98% purity). MS m/z [M+H]+ calc'd for C26H24N2O9, 509.15. found 509.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09120747B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-edc24e9aefdd4ac5842343df0e17054e |
| Source note | uspto-grants-2015_09 |