Difluoroacetic acid → HCID 123185984, compound

HRID 1893606Notes

Reaction equation

HRID 1893606 reaction equation
[NH2:1][C:2](=[N:41][OH:42])[C:3]1[CH:4]=[CH:5][C:6]([CH3:40])=[C:7]([N:9]([CH2:26][C:27]([N:29]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32]2)[CH3:30])=[O:28])[CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH3:18])=[O:12])[CH:8]=1.[F:43][CH:44]([F:48])[C:45](O)=O.CCN=C=NCCCN(C)C>O1CCOCC1.C(OCC)(=O)C.CCCCCC>[F:43][CH:44]([F:48])[C:45]1[O:42][N:41]=[C:2]([C:3]2[CH:4]=[CH:5][C:6]([CH3:40])=[C:7]([N:9]([CH2:26][C:27]([N:29]([N:31]3[CH2:32][C:33]4[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:39]3)[CH3:30])=[O:28])[CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:17][CH3:18])=[O:12])[CH:8]=2)[N:1]=1

Participants

6

Reactant 3

HCID 9788Difluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 123493647HCID 123493647, compound

Product 1

HCID 123185984HCID 123185984, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound (406 mg, 0.698 mmol) of step A, difluoroacetic acid (0.12 ml, 1.90 mmol) and WSC (530 mg, 2.76 mmol) were dissolved in 1,4-dioxane (5 ml) and the mixture was heated under reflux for 5 hr. The reaction mixture was diluted with an ethyl acetate-hexane=1:1 mixed solvent, and the organic layer was washed with water, 10% aqueous citric acid solution, diluted aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane→ethyl acetate-methanol) to give the title compound (97 mg, yield 22%) as a pale-yellow amorphous solid

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr
  3. washthe organic layer was washed with water, 10% aqueous citric acid solution, diluted aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane→ethyl acetate-methanol)

Sources & evidence

ORD record
ord-76bf8dc00fad4904bc50cf8d17dc0c93
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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