HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester | HCID 90000943 | — |
| Reactant | HCID 91658733 | HCID 91658733 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester | HCID 89995945 | — |
Reaction Steps
A mixture of (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester (0.4 g, 1.27 mmol) and diphenylvinylsulfonium triflate (0.5 g, 1.4 mmol) in dichloromethane (10 mL) was added triethylamine dropwise at 0° C. After stirring for 12 hours, the mixture was diluted with water, and then extracted with ethyl acetate, then dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatopraphy (eluented with ethyl acetate/hexane=1:4) to afford the product as a white solid. MS: calc'd (MH+) 342, measured (MH+) 342.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447086B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-9c044b0d60d347c288a633b47d8a2491 |
| Source note | uspto-grants-2016_09 |