Diisopropyl Ether → (E)-3-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]acrylic acid

HRID 499594Notes

Reaction equation

HRID 499594 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[CH:17]=[C:16](/[CH:18]=[CH:19]/[C:20]([O:22]C(C)(C)C)=[O:21])[CH:15]=[CH:14][N:13]=2)=[N:3]1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[CH:17]=[C:16](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH:15]=[CH:14][N:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 59750228tert-Butyl (E)-3-[2-(4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]acrylate

Product 1

HCID 59750225(E)-3-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]acrylic acidYield 64.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (E)-3-[2-(4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]acrylate (0.14 g, 0.44 mmol) was dissolved in trifluoroacetic acid (2.0 ml), and the mixture was stirred at room temperature for 2.5 hrs. Isopropyl ether was added to the reaction mixture to precipitate crystals, which were collected by filtration and recrystallized from tetrahydrofuran-ethanol to give the titled compound (0.088 g, 64%) as white crystals.

Workup

  1. customto precipitate crystals, which
  2. filtrationwere collected by filtration
  3. customrecrystallized from tetrahydrofuran-ethanol

Sources & evidence

ORD record
ord-25f8c0a99f0149519c1d3dab2556b356
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…