HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)-3-(2-Amino-7-isopropyl-4-methyl-benzothiazol-6-ylsulfanyl)-4-hydroxy-6-[2-(4-hydroxyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one | HCID 54682331 | — |
| Reactant | toluene-4-thiosulfonic acid S-(2-amino-7-isopropyl-4-methyl-benzothiazol-6-yl)ester | HCID 86592610 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-3-(2-Amino-7-isopropyl-4-methyl-benzothiazol-6-ylsulfanyl)-4-hydroxy-6-[2-(4-hydroxyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one | HCID 54689397 | — |
Reaction Steps
The title compound was prepared according to General Method 16a using toluene-4-thiosulfonic acid S-(2-amino-7-isopropyl-4-methyl-benzothiazol-6-yl)ester (Example BB-5; 0.35 g, 1.27 mmol), (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (Example J-10; 0.35 g. 1.27 mmol), potassium carbonate (0.7 g), and DMF (5 mL). The crude reaction mixture was purified by flash chromatography (20% EtOAc in hexanes to 50% EtOAc in hexanes to 5% MeOH in EtOAc as eluents), mp 232-234° C. MS (APCI): 513 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06852711B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-59d822f8a46140da8edcf4e033b9238c |
| Source note | uspto-grants-2005_02 |