HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → [Rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 2-[2-(4-Tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethanol | HCID 22647595 | — |
| Reactant | [Rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester | HCID 22708420 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [Rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid ethyl ester | HCID 68616635 | — |
Reaction Steps
In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester was reacted with 2-[2-(4-tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethanol (example 12 b]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid as light yellow amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06809110B2 |
| Source dataset | uspto-grants-2004_10 |
| ORD ID | ord-244431c062f743f5a58c8234f6115400 |
| Source note | uspto-grants-2004_10 |