Trifluoroacetic acid → HCID 67966819, compound

HRID 527516Notes

Reaction equation

HRID 527516 reaction equation
CC([N:5]([C@H:9]([CH3:30])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:25]3[C:26]([CH3:29])=[N:27][O:28][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)=[O:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:29][C:26]1[C:25]2[C:20]([O:19][C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH3:30])[NH2:5])=[CH:14][CH:15]=3)=[CH:21][CH:22]=[CH:23][C:24]=2[O:28][N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698407HCID 86698407, compound2×

Product 1

HCID 67966819HCID 67966819, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl[(1R)-1-methyl-2-({4-[(3-methyl-1,2-benzisoxazol-4-yl)oxy]phenyl}amino)-2-oxoethyl]carbamate (Intermediate 13, 587 mg) was dissolved in 10.0 ml of DCM and then TFA (5.0 ml) was added. The reaction mixture was stirred at room temperature for 1 hour. After the removal of the volatiles, the residue was purified with an SCX cartridge and eluted with DCM/MeOH/NH3 (2.0 M solution in MeOH). Evaporation afforded 337 mg of the title compound.

Workup

  1. customAfter the removal of the volatiles
  2. customthe residue was purified with an SCX cartridge
  3. washeluted with DCM/MeOH/NH3 (2.0 M solution in MeOH)
  4. customEvaporation

Sources & evidence

ORD record
ord-014a2c8bd0f745389e9252f7baa41bca
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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