Trifluoroacetic acid → HCID 85472359, compound

HRID 2177143Notes

Reaction equation

HRID 2177143 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][O:15][C:16]3[C:21]([F:22])=[CH:20][C:19]([CH2:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:18][C:17]=3[F:32])=[C:12]([C:33]([F:36])([F:35])[F:34])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([CH2:14][O:15][C:16]3[C:21]([F:22])=[CH:20][C:19]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:18][C:17]=3[F:32])=[C:12]([C:33]([F:34])([F:35])[F:36])[S:11][N:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90417961Tert-butyl 3-(4-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate

Product 1

HCID 85472359HCID 85472359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask, was placed tert-butyl 3-(4-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)propanoate (520 mg, 0.99 mmol, 1.00 equiv), CF3COOH (2.0 mL), dichloromethane (8.0 mL). The resulting solution was stirred overnight at 25° C. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The solid was washed by EtOAc and hexane. The mixture was filtered and the solid was dried under vacuum. This resulted in 0.37 g (80%) of 3-(4-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl) propanoic acid as a white solid. 1H-NMR (300 Hz, CD3OD): δ 7.67 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 6.86 (d, J=9.6 Hz, 2H), 5.21 (s, 2H), 2.87 (t, J=7.5 Hz, 2H), 2.74 (q, J1=7.5 Hz, J2=15.2 Hz, 2H), 2.61 (t, J=7.8 Hz, 2H), 1.30 (t, J=7.5 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H18F5NO3S, 472.1 (M+H). found 472.1.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washThe solid was washed by EtOAc and hexane
  4. filtrationThe mixture was filtered
  5. customthe solid was dried under vacuum
  6. customThis resulted in 0.37 g (80%) of 3-(4-[[3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl) propanoic acid as a white solid

Sources & evidence

ORD record
ord-d470ea64a897487ba773a63d6c4f07b1
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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