HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → [Rac]-2-ethoxy-3-{3-fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | (4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol | HCID 2783005 | — |
| Reactant | [Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester | HCID 68618019 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [Rac]-2-ethoxy-3-{3-fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester | HCID 68616737 | — |
Reaction Steps
In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with [4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-{3-fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-2-ethoxy-3-{3-fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid as light yellow solid,
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06809110B2 |
| Source dataset | uspto-grants-2004_10 |
| ORD ID | ord-9708cde66b344b4ab9c003693a285fcd |
| Source note | uspto-grants-2004_10 |