HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)-octanoic Acid Tert-butyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (3S,5R)-3-Hydroxymethyl-5-methyl-octanoic Acid Tert-butyl Ester | HCID 57070108 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)-octanoic Acid Tert-butyl Ester | HCID 57178500 | 91.1% |
Reaction Steps
To alcohol 103 (1.98 g, 8.1 mmol) in CH2Cl2 (40 mL) at room temperature was added triethylamine (2.4 g, 0.024 mol), DMAP (20 mg) and tosyl chloride (2.3 g, 0.012 mol). After 14 hours 1N HCl was added and the two layers separated. The aqueous phase was extracted with ether and the combined organic phases dried (MgSO4) and concentrated. Flash chromatography (95% hexane/EtOAc) gave tosylate 104 as an oil (2.94 g, 91%). 13C NMR (100 MHz; CDCl3) 171.60, 144.92, 133.07, 130.02, 128.12, 80.80, 72.15, 39.73, 38.09, 37.89, 32.67, 29.71, 28.22, 21.83, 20.10, 19.54, 14.49.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06642398B2 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-30375e87f8174d31a213184472afdf66 |
| Source note | uspto-grants-2003_11 |