3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 89533687, compound

HRID 1050977Notes

Reaction equation

HRID 1050977 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].[NH2:11][C:12]1[C:13]([F:31])=[C:14]([CH:28]=[CH:29][CH:30]=1)[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[O:16]>CO>[F:31][C:13]1[C:12]([NH:11][C:3]2[C:4](=[O:10])[C:5](=[O:9])[C:6]=2[O:7][CH3:8])=[CH:30][CH:29]=[CH:28][C:14]=1[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[O:16]

Participants

4

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 89533692HCID 89533692, compound

Product 1

HCID 89533687HCID 89533687, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.80 g (0.01 mol; 2.0 eq) of 3,4-dimethoxy-3-cyclobutene-1,2-dione were added to a solution of 1.87 g (0.08 mol; 1.0 eq) of isopropyl (S)-1-(3-amino-2-fluorobenzoyl)pyrrolidine-2-carboxylate in 45 ml of methanol. The reaction medium 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). 1.32 g of isopropyl (S)-1-[2-fluoro-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]pyrrolidine-2-carboxylate were obtained in the form of a light yellow amorphous solid. Yield=51%.

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-0257435a25ec48dd8147833384151f48
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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