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

HRID 499425Notes

Reaction equation

HRID 499425 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-89718b8e270e4238a97b1abc109a8be2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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