Trifluoroacetic acid → HCID 22628189, compound

HRID 278623Notes

Reaction equation

HRID 278623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:27][C:26]([C:28]4[CH:29]=[CH:30][C:31]([NH:34]C(OC(C)(C)C)=O)=[N:32][CH:33]=4)=[N:25][C:24]=3[CH3:42])=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.FC(F)(F)C(O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[S:27][C:26]([C:28]4[CH:29]=[CH:30][C:31]([NH2:34])=[N:32][CH:33]=4)=[N:25][C:24]=3[CH3:42])=[O:22])[CH2:17][CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22628139HCID 22628139, compound

Product 1

HCID 22628189HCID 22628189, compoundYield 88.6%

Procedure

A mixture of 1-(6-chloronaphthalene-2-sulfonyl)-4-(2-(2-tert-butoxycarbonylamino-5-pyridyl)-4-methyl-thiazole-5-carbonyl)piperazine (180 mg) and trifluoroacetic acid (1.0 ml) was stirred at room temperature for 1 hour and concentrated. To the residue was added sodium hydrogen carbonate aqueous solution, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was crystallized from ethyl acetate to give solvate of the title compound (134 mg).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added sodium hydrogen carbonate aqueous solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-13f77c35c5dd49f38ca1a18ee214886b
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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