HuagongsheHuagongshe Chemistry Print Report · For research reference only
PyBroP → 4-(2-((2s,3s)-2-Acetyl-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-oxoethyl)-2-chloro-3-methylbenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | 2-(3-Chloro-4-cyano-2-methylphenyl)acetic acid | HCID 16731996 | — |
| Reactant | Trifluoroacetic acid methylene chloride | HCID 21863450 | — |
| Reactant | (2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)pyrrolidine | HCID 66863428 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(2-((2s,3s)-2-Acetyl-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-oxoethyl)-2-chloro-3-methylbenzonitrile | HCID 16731846 | 50.6% |
Reaction Steps
To compound 1L (480 mg, 1.4 mmol) was added 7 mL of 10% TFA/CH2Cl2 solution at RT, and stirred at 4 hr. A 7 mL toluene was added to the reaction mixture, and concentracted. It was dissolved in 5 mL of CH2Cl2, a solution of PyBrop (1.2 g, 2.5 mmol) and compound 1G (210 mg, 1 mmol) in 3 mL of THF were added followed by iPr2NET (520 μL, 3 mmol), and the stirring was continued for 3 hr at RT. It was concentracted, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Purification by flash chromatography (silica gel, 30% EtOAc in hexanes) provided the title compound (220 mg). MS (ES) m/z 435 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07388027B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-18d88f0a6bb648fb8cbf0a2d5c41ffd3 |
| Source note | uspto-grants-2008_06 |