Trifluoroacetic acid → HCID 86650038, compound

HRID 1892532Notes

Reaction equation

HRID 1892532 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][NH:20][C:21]([NH:23][NH:24]C(OC(C)(C)C)=O)=[O:22])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>ClCCl>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH:20][C:21]([NH:23][NH2:24])=[O:22])=[CH:16][CH:17]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762012HCID 86762012, compound

Product 1

HCID 86650038HCID 86650038, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-{[2-(4-{[2-(acetylamino)-1,3-thiazol-4-yl]methoxy}phenyl)ethyl]carbamoyl}hydrazinecarboxylate (305.0 mg, 0.667 mmol) in anhydrous dichloromethane (20 ml) was added trifluoroacetic acid (2.48 ml, 33.4 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hr,and concentrated under reduced pressure. Dichloromethane (20 ml) was added to the residue and the mixture was concentrated again under reduced pressure. This operation was repeated 3 times to remove trifluoroacetic acid azeotropically. Ethyl acetate (30 ml) was added to the residue and the mixture was stirred. The precipitate was collected by filtration, washed 5 times with ethyl acetate and 5 times with diethyl ether, and dried under reduced pressure to give the title compound (253.4 mg, 0.547 mmol, yield 81.9%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionDichloromethane (20 ml) was added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove trifluoroacetic acid azeotropically
  5. additionEthyl acetate (30 ml) was added to the residue
  6. stirringthe mixture was stirred
  7. filtrationThe precipitate was collected by filtration
  8. washwashed 5 times with ethyl acetate and 5 times with diethyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ef545ed165ee42a68deb2eaf3b464e01
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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