tert-Butyl (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoate → (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoic acid

HRID 499404Notes

Reaction equation

HRID 499404 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[N:17]=[C:16](/[CH:18]=[CH:19]/[C:20]([O:22]C(C)(C)C)=[O:21])[CH:15]=[CH:14][CH:13]=2)=[N:3]1>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[N:17]=[C:16](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

3

Reactant 1

HCID 59750467tert-Butyl (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoate

Product 1

HCID 59750425(E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (E)-3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-propenoate (0.78 g, 2.0 mmol) was dissolved in trifluoroacetic acid (4.0 ml) under ice cooling condition. The reaction mixture was stirred for 1 hr while it was warmed gradually to room temperature. The reaction mixture was concentrated under reduced pressure to precipitate crystals, which were recrystallized from methanol-diisopropyl ether to give the titled compound (0.60 g, 97%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto precipitate crystals, which
  3. customwere recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-3a71c8e2d4b24d02a1c9483d8c937746
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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