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

HRID 499559Notes

Reaction equation

HRID 499559 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-3bcb394803e2422d8b1311d4fccdecf8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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