HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (4R)-1-(5-chloro-3-[2-methoxy-5-(2-piperazin-1-ylethyl)phenyl]-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | tert-butyl 4-{2-[3-(5-chloro-3-{(2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxypyrrolidin-1-yl}-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-methoxyphenyl]ethyl}piperazine-1-carboxylate | HCID 59867855 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (4R)-1-(5-chloro-3-[2-methoxy-5-(2-piperazin-1-ylethyl)phenyl]-1-{[4-methoxy-2-(trifluoromethoxy)phenyl]sulfonyl}-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-L-prolinamide | HCID 59867843 | 56.3% |
Reaction Steps
Concentrated hydrochloric acid (3.0 ml) was added to 120 mg of the compound obtained in Example 228, and the solution was stirred at room temperature for 30 minutes. The stirred solution was poured into a saturated aqueous solution of NaHCO3, and extraction was carried out with EtOAc. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by a preparative TLC plate (2 mm; mobile phase: CHCl3/8M ammonia MeOH solution=8/1; v/v) to obtain 60 mg of the title compound (colorless amorphous).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030499B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-640f983aed2849969315d45b81ad7513 |
| Source note | uspto-grants-2011_10 |