HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | 1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid methyl ester | HCID 69894795 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid | HCID 22646741 | 69.5% |
Reaction Steps
1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-cyclohexanecarboxylic acid methyl ester (0.40 g) and lithium hydroxide monohydrate (0.20 g) were combined in tetrahydrofuran (20 ml), methanol (10 ml) and water (5 ml) and heated to reflux for 10 h. The organic solvents were then removed under reduced pressure. The aqueous residue was diluted with water (20 ml), acidified with citric acid to approximately pH 4, and a white precipitate filtered off. After drying, the precipitated solid was triturated with hot ethyl acetate (30 ml) to provide the title compound as a white solid (0.27 g, 69%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06787536B2 |
| Source dataset | uspto-grants-2004_09 |
| ORD ID | ord-d41dd7cc6b504b22aacc338455dfcf08 |
| Source note | uspto-grants-2004_09 |