HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 3-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester | HCID 69231016 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid | HCID 17984324 | 18% |
Reaction Steps
This ester intermediate was dissolved in THF (0.6 mL) and MeOH (0.4 mL) and treated with aqueous 2M LiOH (1.0 mL, 2.0 mmol). The mixture was stirred for 16 h at ambient temperature, neutralized with HCl (1.0 mL, 2.0 M), and concentrated. The residue was extracted with EtOAc (3×5 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified using silica gel chromatography column (hexanes/EtOAc/HOAc, 5/5/0.02) to afford the title compound (10 mg, 18%). MS (ES+) m/z 566.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07282501B2 |
| Source dataset | uspto-grants-2007_10 |
| ORD ID | ord-7f1242fdc81f422d9bba3ce013007223 |
| Source note | uspto-grants-2007_10 |