Hydrochloric Acid → 2-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester

HRID 226538Notes

Reaction equation

HRID 226538 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][O:17][C:18](=[O:42])[CH:19]([C:24]1[CH:25]=[C:26]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=2)[CH:27]=[C:28](O)[CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22].N1C=CC=CC=1.Cl>C(Cl)Cl>[CH3:16][O:17][C:18](=[O:42])[CH:19]([C:24]1[CH:25]=[C:26]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([F:41])([F:39])[F:40])[CH:32]=2)[CH:27]=[C:28]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 577549272-(4'-Chloro-5-hydroxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester

Product 1

HCID 577549642-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl esterYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulphonic anhydride (93 μL, 0.57 mmol) was added dropwise to a stirred solution of 2-(4′-chloro-5-hydroxy-3′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (prepared in Example A) (150 mg, 0.38 mmol) and pyridine (88 μL, 1.1 mmol) in DCM (3 mL) at 0° C. The reaction was warmed to room temperature and stirred for 1 h, then 1M hydrochloric acid was added. The organic layer was filtered through a polytetrafluoroethylene (PTFE) frit and concentrated in vacuo to give the title compound (205 mg, 100%) as an orange oil.

Workup

  1. filtrationThe organic layer was filtered through a polytetrafluoroethylene (PTFE) frit
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a17f1c82f314fe0821be8583b4be693
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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