Diisopropyl Ether → {Methyl[6-(4-oxo-1,3-benzothiazin-2-yl)-2-pyrazinyl]amino}acetic acid

HRID 748378Notes

Reaction equation

HRID 748378 reaction equation
[CH3:1][N:2]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:3]1[CH:8]=[N:7][CH:6]=[C:5]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[N:4]=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[CH3:1][N:2]([CH2:20][C:21]([OH:23])=[O:22])[C:3]1[CH:8]=[N:7][CH:6]=[C:5]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[N:4]=1

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 59750128tert-Butyl {methyl[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyrazinyl]amino}acetate

Product 1

HCID 59750201{Methyl[6-(4-oxo-1,3-benzothiazin-2-yl)-2-pyrazinyl]amino}acetic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl {methyl[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyrazinyl]amino}acetate (0.20 g, 0.52 mmol) was dissolved in trifluoroacetic acid (5 ml), and the mixture was stirred for 0.5 hr. Diisopropyl ether was added thereto. The obtained precipitates were recrystallized from ethanol to give the titled compound (0.15 g, 87%) as pale yellow crystals

Workup

  1. customThe obtained precipitates
  2. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-dea045d4003e4b84802d2694fe8baffb
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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