HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Toluenesulfonyl chloride → Methyl(4S)-4-[(tert-butoxy)carbonylamino]-5-[(4-methylphenyl)sulfonyloxy]pentanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate | HCID 11107667 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl(4S)-4-[(tert-butoxy)carbonylamino]-5-[(4-methylphenyl)sulfonyloxy]pentanoate | HCID 15933198 | 54.2% |
Reaction Steps
Methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate (9.11 mmol, 2.25 g) was dissolved in 30 mL of methylene chloride. p-Toluenesulfonyl chloride (9.1 mmol, 1.7 g) and triethylamine (27.33 mmol, 3.8 mL) were added and the reaction was stirred at room temperature overnight. Solvent was removed in vacuo and crude was purified by column chromatography (SiO2, 4:1 n-hexanes/ethyl acetate to 7:3 n-hexanes/ethyl acetate) to yield the title compound (1.98 g, 54% yield). ES-MS: 402 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101588B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-be7bafcaa5864bf297d09f01fc2521c9 |
| Source note | uspto-grants-2012_01 |