HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Fluorophenol → (S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Fluorophenol | HCID 9732 | — |
| Reactant | Methyl thiocyanate | HCID 11168 | — |
| Reactant | Boron Trichloride | HCID 25135 | — |
| Reactant | D-Cysteine | HCID 92851 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | (S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid | HCID 136411678 | — |
Reaction Steps
(S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid (5′-fluorodesazadesmethylDFT, 29a) is prepared from the cyclization of D-cysteine onto 5-fluoro-2-hydroxybenzonitrile in slightly acidic buffer. The aromatic precursor could be made by direct cyanation of p-fluorophenol using methyl thiocyanate, aluminum chloride, and boron trichloride in ethylene dichloride followed by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06864270B2 |
| Source dataset | uspto-grants-2005_03 |
| ORD ID | ord-8d305a17bda041948afaccf7ffaa9077 |
| Source note | uspto-grants-2005_03 |