Trifluoroacetic acid → HCID 69218024, compound

HRID 1393101Notes

Reaction equation

HRID 1393101 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([N:14](C(OC(C)(C)C)=O)[CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH3:31])=[CH:9][C:8]=1[CH3:39])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([NH:14][CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=3)=[N:18][C:17]=2[CH3:31])=[CH:9][C:8]=1[CH3:39])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69217715HCID 69217715, compound

Product 1

HCID 69218024HCID 69218024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.360 g (0.62 mmol) of the above prepared (4-{tert-butoxycarbonyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-2,6-dimethyl-phenoxy)-acetic acid ethyl ester was dissolved in 6.25 ml of CH2Cl2 and treated dropwise with 1.59 ml of TFA (33 eq.). After additional 30 min at RT, the bulk of the solvents was removed i. V. and the residue distributed between cold NaHCO3-solution and EtOAc. Washing of the organic layer with cold water and brine, drying over magnesium sulfate, and evaporation of the solvents left 0.292 g of the title compound as off-white solid which was used as such for the next step, MS: 479.4 (MH)+.

Workup

  1. customthe bulk of the solvents was removed i
  2. washWashing of the organic layer with cold water and brine
  3. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  4. waitleft 0.292 g of the title compound as off-white solid which

Sources & evidence

ORD record
ord-15a0e92294e1433da070ab2d1d482bba
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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