HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Borane | HCID 6331 | — |
| Reactant | (r)-3-(2-Nitro-4-sulfamoylphenylamino)-4-(phenylthio)butanoic acid | HCID 11683013 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(((1r)-3-Hydroxy-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide | HCID 68453593 | — |
Reaction Steps
A mixture of Example 122E (206 mg, 0.50 mmol) and 1M borane in THF (20 mL) was stirred for 16 hours, treated sequentially with methanol (5.0 mL) and 1N HCl (2.0 mL), diluted with ethyl acetate (50 mL), washed with water (2 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/dichloromethane to provide the desired product. MS (ESI(+)) m/e 398 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07754886B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-7d53a8d5a21a40228c5df673f439e864 |
| Source note | uspto-grants-2010_07 |