Sodium Chloride → HCID 54404256, compound

HRID 1870823Notes

Reaction equation

HRID 1870823 reaction equation
FC(F)(F)C(O)=O.CS(O)(=O)=O.C(O[C:16]([C:31]1[CH:35]=[C:34]([N:36]=[C:37]([NH2:44])[N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[O:33][N:32]=1)([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:20]([F:30])[CH:19]=1)[CH3:17])C.[Cl-].[Na+]>C(Cl)Cl>[F:30][C:20]1[CH:19]=[C:18]([C:16]([C:31]2[CH:35]=[C:34]([N:36]=[C:37]([NH2:44])[N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)[O:33][N:32]=2)=[CH2:17])[CH:23]=[CH:22][C:21]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 86755587HCID 86755587, compound

Product 1

HCID 54404256HCID 54404256, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 ml) was added to a solution of the compound (30.0 mg) obtained in Example 53 in methylene chloride (1 ml), and the resulting mixture was stirred at room temperature for 8 hours. After the addition of a saturated aqueous sodium chloride solution, the mixture was subjected to extraction with ethyl acetate, and the organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, thereafter dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography to obtain the desired compound (20 mg).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washthe organic layer was washed successively with a saturated aqueous sodium bicarbonate solution
  3. dry with materiala saturated aqueous sodium chloride solution, thereafter dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-346a459849d6400685d95e6baedac42e
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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