Trifluoroacetic acid → (4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

HRID 546951Notes

Reaction equation

HRID 546951 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:53])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:49][CH3:50])([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][C:35]([O:44]COC)([C:40]([F:43])([F:42])[F:41])[C:36]([F:39])([F:38])[F:37])=[C:29]([CH3:48])[CH:28]=3)[CH2:25][CH3:26])=[CH:20][C:19]=2[CH3:51])=[CH:14][C:13]=1[F:52]>ClCCl>[CH3:8][O:9][C:10](=[O:53])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:49][CH3:50])([C:27]3[CH:32]=[CH:31][C:30]([C:33]#[C:34][C:35]([OH:44])([C:40]([F:41])([F:43])[F:42])[C:36]([F:38])([F:37])[F:39])=[C:29]([CH3:48])[CH:28]=3)[CH2:25][CH3:26])=[CH:20][C:19]=2[CH3:51])=[CH:14][C:13]=1[F:52]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57709061(4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

Product 1

HCID 57708915(4'-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (1.5 mL) and trifluoroacetic acid (0.153 mL) were added to (4′-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 78-(1); 41 mg, 0.063 mmol), and the mixture was stirred at room temperature for one day. The reaction solution was directly concentrated under reduced pressure and azeotropically distilled with toluene. The residue was purified by preparative TLC (hexane/ethyl acetate=5/1) to give the title compound (30.1 mg, 79%).

Workup

  1. concentrationThe reaction solution was directly concentrated under reduced pressure
  2. distillationazeotropically distilled with toluene
  3. customThe residue was purified by preparative TLC (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-8e95e5fffff4478b906c751b26fdf508
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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