HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 2-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 9H-fluoren-9-ylmethyl ester | HCID 10881773 | — |
| Reactant | 2-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester | HCID 59759449 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-{[4-(2-{[(9H-fluorene-9-ylmethoxy)carbonyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester | HCID 59759401 | 100.1% |
Reaction Steps
To a solution of 2-{[4-(2-aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (19 g) synthesized in Example 7 in tetrahydrofuran (60 mL) was added N-(9H-fluorene-9-ylmethyloxycarbonyl)succinimide (23 g), and the mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and saturated brine. The precipitate was filtered and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (33 g) as a pale-brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08026370B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-e54a07513fed49f9911356b691489a25 |
| Source note | uspto-grants-2011_09 |