3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 89534499, compound

HRID 1528203Notes

Reaction equation

HRID 1528203 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]([O:19][CH3:20])=[O:18])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[CH3:21][O:22][C:23]1[C:24](=O)[C:25](=[O:29])[C:26]=1[O:27]C>CO>[CH3:21][O:22][C:23]1[C:26](=[O:27])[C:25](=[O:29])[C:24]=1[NH:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]([O:19][CH3:20])=[O:18])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 131733213HCID 131733213, compound

Product 1

HCID 89534499HCID 89534499, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.54 g of methyl (R)-1-(3-amino-4-chlorobenzenesulfonyl)pyrrolidine-2-carboxylate and 5.68 g of 3,4-dimethoxycyclobut-3-ene-1,2-dione in 50 ml of methanol was heated at 60° C. overnight. The solvent was evaporated off and the residue was chromatographed on silica gel eluted with heptane/ethyl acetate (4:1, 2:1, and pure ethyl acetate). 0.92 g of methyl (R)-1-[3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzenesulfonyl]pyrrolidine-2-carboxylate was obtained. Yield=23%.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was chromatographed on silica gel
  3. washeluted with heptane/ethyl acetate (4:1, 2:1, and pure ethyl acetate)

Sources & evidence

ORD record
ord-af56f617229b40808aa9bf1c534f7589
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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