HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Anhydride → N-((SR)-2-((3SR,5RS,6SR)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | (3SR,5RS,6SR)-3-allyl-1-((SR)-1-aminobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one | HCID 67999439 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-((SR)-2-((3SR,5RS,6SR)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butyl)acetamide | HCID 68000611 | — |
Reaction Steps
To a solution of 53 mg (0.123 mmol) of (3SR,5RS,6SR)-3-allyl-1-((RS)-1-aminobutan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one (Step B) in DMF (307 μL) was added acetic anhydride (116 μL, 1.229 mmol) at 25° C. After being stirred at 25° C. for 14h the reaction was quenched (H2O) and extracted (2×EtOAc). The combined organic layers were washed with sat. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Separation by reversed phase HPLC (50 to 80% AcCN/H2O in 25 min, 2 injections, tR=15.683 min) provided the title compound as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09296736B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-059121bac9d14dc5b861674524477abd |
| Source note | uspto-grants-2016_03 |