HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | (S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester | HCID 67074039 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | (S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester | HCID 86638111 | 108.8% |
Reaction Steps
A solution of (S)-2-[benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester (26.0 g, 80.0 mmol) and pyridinium toluene-4-sulfonate (10.0 g, 40.0 mmol) in 2-butanone (260 mL) and water (8.6 mL, 0.48 mol) was heated under reflux for 16 h, then the solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (24.3 g), which was directly used in the next step. Yellow oil, MS (ISP)=348.3 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071586B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-4b3a9428721846aeaa2780f1ac2d74ea |
| Source note | uspto-grants-2011_12 |