HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 12049888, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | P-Hydroxynorephedrine | HCID 6931143 | — |
| Reactant | Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate | HCID 12049887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 12049888 | HCID 12049888 | 31.7% |
Reaction Steps
A solution of (1R,2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (97 mg), ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate (187 mg) and N,N-diisopropylethylamine (203 μl) in N,N-dimethylformamide (3 ml) was stirred for 10 hours at 60° C. After cooling, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo, purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=30/1) gave ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethyl]amino]ethyl]phenoxy]acetate (75 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06399660B1 |
| Source dataset | uspto-grants-2002_06 |
| ORD ID | ord-2e0b8f37b70b425cb70cc37ae43b6a59 |
| Source note | uspto-grants-2002_06 |