4-Chlorobenzenesulfonyl chloride → (3R)-1-[(4-chlorophenyl)sulfonyl]-3-methylpiperazine

To a solution of 1,1-dimethylethyl (2R)-2-methyl-1-piperazinecarboxylate (1.5 g, 07.5 mmol) in dry DCM (40 mL) was added triethylamine (2.59 mL, 18.8 mmol) and 4-chlorobenzenesulfonyl chloride (3.15 g, 10.5 mmol) and the reaction stirred at room temperature for 48 h. To the reaction was added resin supported-triamine (5 g) and the mixture stirred for 4 h. The reaction mixture was filtered and the filtrate washed with 0.5 M HCl (aq., 100 mL) followed by water (100 mL) before it was dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was dissolved in DCM (40 mL) and TFA (10 mL) was added. The solution was stirred for 20 min. The solvent was evaporated and the residue tajen up in DCM (40 mL) and washed with 50% aqueous sodium bicarbonate (100 mL) followed by water (100 mL). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound (1.62 g).

1. additionTo the reaction was added resin
2. stirringthe mixture stirred for 4 h
3. filtrationThe reaction mixture was filtered
4. washthe filtrate washed with 0.5 M HCl (aq., 100 mL)
5. dry with materialwas dried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. dissolutionThe crude product was dissolved in DCM (40 mL)
9. additionTFA (10 mL) was added
10. stirringThe solution was stirred for 20 min
11. customThe solvent was evaporated
12. washthe residue tajen up in DCM (40 mL) and washed with 50% aqueous sodium bicarbonate (100 mL)
13. dry with materialThe organic phase was dried (MgSO4)
14. filtrationfiltered
15. customthe solvent removed in vacuo

ORDレコード

ord-d72421402bcd411a95caa05e81703400

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530478B2