Trifluoroacetic acid → 1-[2-Carboxy-4-(pyridin-4-yl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

HRID 352902Notes

Reaction equation

HRID 352902 reaction equation
Cl.C([O:6][C:7]([C:9]1[CH:36]=[C:35]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][C:10]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([Cl:32])[CH:28]=3)[CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1)=[O:12])=[O:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:7]([C:9]1[CH:36]=[C:35]([C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][C:10]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([Cl:32])[CH:28]=3)[CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1)=[O:12])([OH:8])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 227107461-[2-tert-Butoxycarbonyl-4-(pyridin-4-yl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride

Product 1

HCID 227108661-[2-Carboxy-4-(pyridin-4-yl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazineYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (50 ml), 1-[2-tert-butoxycarbonyl-4-(pyridin-4-yl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride (250 g) was dissolved, followed by the dropwise addition of trifluoroacetic acid (50 ml) under ice cooling. After stirring at room temperature for 5 hours, the solvent was distilled off. The residue was dissolved in methanol and the resulting solution was allowed to stand in a refrigerator for one day. The colorless solid so precipitated was collected by filtration and dried, whereby the title compound (550 mg, 28%) was obtained as a colorless solid.

Workup

  1. distillationthe solvent was distilled off
  2. dissolutionThe residue was dissolved in methanol
  3. waitto stand in a refrigerator for one day
  4. customThe colorless solid so precipitated
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-e394ed86b5f44f4695320c2b65c37c01
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…