Trifluoroacetic acid → HCID 57809813, compound

HRID 2105996Notes

Reaction equation

HRID 2105996 reaction equation
[F:1][C:2]([F:50])([F:49])[C:3]([CH2:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[N:29]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=[CH:20]1)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].FC(F)(F)C(O)=O>C(Cl)Cl>[F:50][C:2]([F:1])([F:49])[C:3]([CH2:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[NH:29])[CH:21]=[CH:20]1)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 57809883HCID 57809883, compound

Product 1

HCID 57809813HCID 57809813, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[4-(tritylimino)-4H-quinolin-1-ylmethyl]pentan-2-ol (470 mg) in methylene chloride (50 mL) was added trifluoroacetic acid (2 mL). After 2 hours, another portion of trifluoroacetic acid (1 mL) was added and the mixture was stirred for another 4 hours. The reaction was quenched by slow addition of saturated aqueous sodium bicarbonate solution and was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 8 to 10% methanol-methylene chloride) to give the title compound (84.2 mg), m.p. 137° C.-140° C.

Workup

  1. customThe reaction was quenched by slow addition of saturated aqueous sodium bicarbonate solution
  2. extractionwas extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography with silica gel (eluted with 8 to 10% methanol-methylene chloride)

Sources & evidence

ORD record
ord-7ebe3dadf05342b2b3545351d91984c0
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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