Diisopropyl Ether → 1-{3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl}proline

HRID 748417Notes

Reaction equation

HRID 748417 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]([CH2:18][CH2:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH:23]3[C:27]([O:29]C(C)(C)C)=[O:28])=[O:21])[CH:15]=[CH:14][CH: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[N:17]=[C:16]([CH2:18][CH2:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][C@H:23]3[C:27]([OH:29])=[O:28])=[O:21])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 22939468tert-Butyl 1-{3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl}-2-pyrrolidinecarboxylate

Product 1

HCID 684582621-{3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl}prolineYield 46.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 1-{3-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl}-2-pyrrolidinecarboxylate (0.25 g, 0.68 mmol) was dissolved in trifluoroacetic acid (2 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 ethanol-hexane to give the titled compound (0.13 g, 45%) as white crystals.

Workup

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

Sources & evidence

ORD record
ord-64cbc3c6162c43bb831f3c8aa00beb08
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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