Trifluoroacetic acid → HCID 67343323, compound

HRID 1669316Notes

Reaction equation

HRID 1669316 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:9]=[CH:10][C:11]([C:14]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67342557HCID 67342557, compound

Product 1

HCID 67343323HCID 67343323, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{4-[1-hydroxy-1-(4′-trifluoromethyl-biphenyl-4-yl)-heptyl]-benzoylamino}-propionic acid methyl ester (150 mg, 0.277 mmol) in dichlorormethane (10 mL) is added TFA (160 mg, 1.4 mmol). 5 min later, triethylsilane (161 mg, 1.4 mmol) is added dropwise. 5 h later, the reaction mixture is diluted with ethyl acetate, washed with 1N NaOH, water, brine, dried over sodium sulfate, concentrated and purified by column chromatography to give the title compound (40 mg).

Workup

  1. washwashed with 1N NaOH, water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-0f04e05c5e11409d86e5b602a03d5107
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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