HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Methyl(+/-)-4-[4-[2-(6-Methylaminopyridin-2-yl)-1-ethoxy]phenyl]-3-(5-methylthiazol2-yl)butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoate | HCID 20775669 | — |
| Reactant | 6-(Methylamino)-2-pyridylethanol | HCID 22319465 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | Methyl(+/-)-4-[4-[2-(6-Methylaminopyridin-2-yl)-1-ethoxy]phenyl]-3-(5-methylthiazol2-yl)butanoate | HCID 22496022 | 106.4% |
Reaction Steps
Diisopropyl azodicarboxylate (0.25 mL, 1.28 mmole) was added to a suspension of methyl (±)-4-(4-hydroxyphenyl)-3-(5-methylthiazol-2-yl)butanoate (249 mg, 0.85 mmole), 6-(methylamino)-2-pyridylethanol (194 mg, 1.28 mmole), and triphenylphosphine (336 mg, 1.28 mmole) in TBME (5 mL) at 0° C. The mixture was allowed to warm to RT as the bath warmed. After 72 hr the mixture was concentrated and the residue was chromatographed on silica gel (30% EtOAc/CHCl3). Fractions containing the product were concentrated to give the title compound (385 mg, contaminated with triphenylphosphine oxide): MS (ES) m/e 426 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06881736B1 |
| Source dataset | uspto-grants-2005_04 |
| ORD ID | ord-f421b1fa64c64b5888d1534b933a8a7e |
| Source note | uspto-grants-2005_04 |