Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 178460591 | HCID 178460591 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178460592 | HCID 178460592 | 15.9% |
Reaction Steps
2-[4-(4-Oxothiolan-3-ylmethyl)phenyl]thiopropionic acid (100 mg) obtained in Example 11 was dissolved in tetrahydrofuran (5.0 ml), and to the solution was added sodium borohydride (16.2 mg) under ice cooling, and then the reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, to the reaction mixture was added 0.5 M aqueous sulfuric acid, and the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the compounds of Example 12-A (pale brown oil, 16 mg, 15.9%) and Example 12-B (colorless oil, 12 mg, 11.9%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08148421B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-c22f74e337914bfbb451f082f1d1bb07 |
|---|
| Source note | uspto-grants-2012_04 |
|---|