Sulfuric Acid → HCID 68448048, compound

HRID 2233192Notes

Reaction equation

HRID 2233192 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:18])([C:15]([OH:17])=[O:16])[C:3]=1[C:4]=23.F[C:20]1C(C2(C([O-])=O)CO2)=C2C(=CC=1)N=CC(OC)=N2.S(=O)(=O)(O)O>CO>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6](=[O:12])[N:5]3[CH2:13][C:14]([OH:18])([C:15]([O:17][CH3:20])=[O:16])[C:3]=1[C:4]=23

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 68447708HCID 68447708, compoundHCID 86628363HCID 86628363, compound

Product 1

HCID 68448048HCID 68448048, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3:1 mixture of 7-fluoro-6-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[1,2,3-de]quinoxaline-6-carboxylic acid and 2-[6-fluoro-3-(methyloxy)-5-quinoxalinyl]-2-oxiranecarboxylate (3.05 g) was partially dissolved in methanol (100 mL) and treated with concentrated sulphuric acid (1 mL), added dropwise at room temperature. The reaction mixture was stirred for 17 hours then quenched to pH 7 by addition of MP-carbonate resin. The mixture was filtered and evaporated. The residue was placed directly onto the top of a 100 g silica gel column and chromatographed, eluting with a 0-50% methanol in ethyl acetate gradient to afford the product (0.558 g, 17% (23% based on acid starting material).

Workup

  1. additionadded dropwise at room temperature
  2. customthen quenched to pH 7 by addition of MP-carbonate resin
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. customchromatographed
  6. washeluting with a 0-50% methanol in ethyl acetate gradient
  7. customto afford the product (0.558 g, 17% (23% based on acid starting material)

Sources & evidence

ORD record
ord-56e0d1bef69d4bd080ac28f58310d187
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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