Trifluoroacetic acid → HCID 24959769, compound

HRID 1430627Notes

Reaction equation

HRID 1430627 reaction equation
C([O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([CH3:24])([C:16](=[O:23])[NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH3:15])[CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:24][C:14]([C:16](=[O:23])[NH:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1)([O:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([OH:25])=[O:5])[CH3:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59363819HCID 59363819, compound

Product 1

HCID 24959769HCID 24959769, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-[1-Methyl-1-(thiazol-2-ylcarbamoyl)-ethoxy]-benzoic acid tert-butyl ester (0.1 g, 0.275 mmol) in DCM (2 ml) a solution of TFA (3 ml) in DCM (3 ml) was added at 0° C. for 15 min. Reaction mixture was stirred at RT for 1 h, diluted with DCM (10 ml) washed with brine (2×4 ml) dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. The crude product was triturated with hexane to obtain white solid, filtered and dried to obtain 3-[1-Methyl-1-(thiazol-2-ylcarbamoyl)-ethoxy]-benzoic acid (0.06 g, 85%). 3-[1-Methyl-1-(thiazol-2-ylcarbamoyl)-ethoxy]-benzoic acid.

Workup

  1. customReaction mixture
  2. washwashed with brine (2×4 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto obtain crude product
  6. customThe crude product was triturated with hexane
  7. customto obtain white solid
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-86b14e1482414cff910a12e6dfd8dca9
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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