Trifluoroacetic acid → HCID 86670454, compound

HRID 1972701Notes

Reaction equation

HRID 1972701 reaction equation
[C:1]1([S:7]([CH2:10][C@@H:11]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[Cl:47][C:48]1[N:53]=[CH:52][C:51]([S:54](Cl)(=[O:56])=[O:55])=[CH:50][CH:49]=1>C(Cl)Cl>[Cl:47][C:48]1[N:53]=[CH:52][C:51]([S:54]([N:13]2[CH2:14][CH2:15][N:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:29])([F:31])[F:30])[C:24]([F:26])([F:25])[F:27])=[CH:19][CH:18]=3)[C@@H:11]([CH2:10][S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])[CH2:12]2)(=[O:56])=[O:55])=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 86670455HCID 86670455, compound

Product 1

HCID 86670454HCID 86670454, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 20 mL vial was charged with tert-butyl (3R)-3-((phenylsulfonyl)methyl)-4-(4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-piperazinecarboxylate (0.038 g, 0.065 mmol), TFA (0.50 mL, 6.5 mmol, Sigma-Aldrich, St. Louis, Mo.) and DCM (1 mL). The mixture was stirred at rt for 10 min. The volatile was removed and the residue was taken into DCM (1 mL). TEA (0.10 mL, 0.78 mmol) was added and the mixture was stirred at rt for 5 min. At this time, 6-chloropyridine-3-sulfonyl chloride (0.016 g, 0.073 mmol, Organic Process Research & Development 2009, 13, 875) was added and the mixture was stirred at rt for 10 min. The reaction mixture was directly purified by column chromatography (10 g of silica, 0 to 50% EtOAc in hexanes) to afford 2-(4-((2R)-4-((6-chloro-3-pyridinyl)sulfonyl)-2-((phenylsulfonyl)methyl)-1-piperazinyl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (0.026 g) as a white solid.

Workup

  1. customThe volatile was removed
  2. stirringthe mixture was stirred at rt for 5 min
  3. stirringthe mixture was stirred at rt for 10 min
  4. customThe reaction mixture was directly purified by column chromatography (10 g of silica, 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4394eb271af6427ab7b453df1a3c5c3e
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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