HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | L-Isoserine | HCID 6999797 | — |
| Reactant | Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate | HCID 86709142 | — |
| Solvent | Sodium Methoxide | HCID 10942334 | — |
| Product | 2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid | HCID 71735140 | 93.5% |
Reaction Steps
A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (90 mg, 0.31 mmol) and 2-(S)-hydroxy-3-amino-propionic acid (Sigma-Aldrich) (96 mg, 0.92 mmol) in 0.5 N NaOMe in MeOH solution (1.22 mL, 0.61 mmol) was microwaved at 120° C. for 1 h and concentrated. Residue was dissolved in water (70 mL) and acidified by 1 N HCl solution to pH=3-4. It was extracted with EtOAc, Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (105 mg, 0.29 mmol) in 92% yield. LC-MS ESI−: 366.99 (M−1)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409892B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-316329ae4d7643ca975d302c89961bdf |
| Source note | uspto-grants-2016_08 |