Trifluoroacetic acid → HCID 67343323, compound

HRID 1669283Notes

Reaction equation

HRID 1669283 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>ClCCl>[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 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{4-[1-Hydroxy-1-(4′-trifluoromethyl-biphenyl-4-yl)-heptyl]-benzoylamino}-propionic acid methyl ester (150 mg, 0.28 mmol) in dichlormethane (10 mL) is added TFA (160 mg, 1.4 mmol) dropwise, followed by the addition of triethylsilane (161 mg, 1.4 mmol). After 2 h, the reaction is quenched by 1N HCl, extracted with ethyl acetate, dried, concentrated, and purified by column chromatography to afford the titled compound (130 mg).

Workup

  1. customthe reaction is quenched by 1N HCl
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-a77cc543b6bf4efb823e22e1c66f0484
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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