Trifluoroacetic acid → 3-[6-(4-Oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acid

HRID 748243Notes

Reaction equation

HRID 748243 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:6]=2[S:5][C:4]([C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:19]=[CH:18][CH:17]=2)=[N:3]1.FC(F)(F)C(O)=O>>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([F:14])([F:13])[F:15])=[CH:11][C:6]=2[S:5][C:4]([C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:19]=[CH:18][CH:17]=2)=[N:3]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22939516tert-Butyl 3-[6-(4-oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate

Product 1

HCID 597503973-[6-(4-Oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propionic acidYield 88.7%

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl 3-[6-(4-oxo-7-trifluoromethyl-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoate (0.35 g, 0.8 mmol) and trifluoroacetic acid (5.0 ml) was stirred at 0° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure and combined with diisopropyl ether to precipitate crystals, which were collected by filtration and dried to give the titled compound (0.27 g, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto precipitate crystals, which
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-82e8f7fc000e448e8b20714f9e46fba1
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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