Trifluoroacetic acid → HCID 44587843, compound

HRID 1857560Notes

Reaction equation

HRID 1857560 reaction equation
[CH2:1]([O:8][CH:9]([C:22]([O-:24])=[O:23])[C@@H:10]([C:19]([O-:21])=[O:20])[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([O:8][CH:9]([C:22]([OH:24])=[O:23])[C@@H:10]([C:19]([OH:21])=[O:20])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86756038HCID 86756038, compound

Product 1

HCID 44587843HCID 44587843, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 65 mg (0.14 mmol) of the compound (14) in chloroform (2 ml) was added 2 ml of trifluoroacetic acid, and then the mixture was stirred at room temperature for 20 hours. The solvent was distilled off and the residue was subjected to column chromatography on ion exchange resin (Dowex 50Wx4) and washed with water, then eluted with 1N aqueous ammonia to give 23 mg of the title compound (15) (yield 65%).

Workup

  1. distillationThe solvent was distilled off
  2. washwashed with water
  3. washeluted with 1N aqueous ammonia

Sources & evidence

ORD record
ord-62e13400eddd41a59e1b8d6c54a9b5bf
Source dataset
uspto-grants-2000_11
Patent number
US06147113

Reaction notes

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