3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → Methyl {[2-hydroxy-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]methylamino}acetate

HRID 1528213Notes

Reaction equation

HRID 1528213 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][NH:5][CH2:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:9]=1[OH:15].[CH3:18][O:19][C:20]1[C:21](=O)[C:22](=[O:26])[C:23]=1[O:24]C>>[OH:15][C:9]1[C:10]([NH:14][C:21]2[C:22](=[O:26])[C:23](=[O:24])[C:20]=2[O:19][CH3:18])=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]([CH2:6][NH:5][CH2:4][C:3]([O:2][CH3:1])=[O:17])=[O:16]

Participants

3

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 131733216Methyl[(3-amino-2-hydroxybenzoyl)methylamino]acetate

Product 1

HCID 131733218Methyl {[2-hydroxy-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]methylamino}acetateYield 61.1%

Procedure

A mixture of 3.92 g (16.4 mmol, 1 eq) of methyl[(3-amino-2-hydroxybenzoyl)methylamino]acetate and 4.68 g (32.9 mmol, 1 eq) of 3,4-dimethoxy-3-cyclobutene-1.2-dione was stirred at ambient temperature for 24 hours. The solvent was evaporated off and the residue was chromatographed on silica gel (200 g prepacked column, eluent 20/80 then 0/100 heptane/ethyl acetate). 3.49 g of methyl {[2-hydroxy-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]methylamino}acetate were obtained in the form of a white solid. Yield=61%.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was chromatographed on silica gel (200 g prepacked column, eluent 20/80

Sources & evidence

ORD record
ord-309267a0ab184f36bbf76aaa745bb85b
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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