HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Toluenesulfonyl chloride → (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2R,3S)-Methyl 2-amino-3-hydroxy-4-methylpentanoate | HCID 89995944 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester | HCID 90000943 | — |
Reaction Steps
A mixture of (2S,3R)-2-amino-3-hydroxy-4-methyl-pentanoic acid methyl ester (0.50 g, 3.4 mmol) and triethylamine (0.69 g, 6.8 mmol) in dichloromethane (10 mL) was added 4-methyl-benzenesulfonyl chloride (0.71 g, 3.7 mmol) at 0° C. After stirring for 2 hours at room temperature, the mixture was washed with water and the organic layer was separated and then dried over sodium sulfate. After removal of solvent, the residue was used in next step without purification. MS: calc'd (MH+) 316, measured (MH+) 316.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447086B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-14ebf1bd860147438186f01ac5e90a16 |
| Source note | uspto-grants-2016_09 |