Diethyl squarate → HCID 89526361, compound

HRID 1528196Notes

Reaction equation

HRID 1528196 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:16]([O:18][C:19]1[C:20](=O)[C:21](=[O:26])[C:22]=1[O:23]CC)[CH3:17]>C(O)C>[CH2:16]([O:18][C:19]1[C:22](=[O:23])[C:21](=[O:26])[C:20]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[O:9])[CH:3]=1)[CH3:17]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 62916971HCID 62916971, compound

Product 1

HCID 89526361HCID 89526361, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the 30 ml of the solution of (3-aminophenyl)-(3-hydroxypyrrolidin-1-yl)methanone in ethanol and 6.81 g of 3,4-diethoxycyclobut-3-ene-1,2-dione (40.0 mmol, 2.5 eq) was heated at 60° C. overnight. The reaction medium was evaporated and the residue was chromatographed on silica gel eluted with heptane/ethyl acetate at 4/1, 2:1, then dichloromethane/methanol (6%). 3.03 g of 3-ethoxy-4-[3-(3-hydroxypyrrolidine-1-carbonyl)phenylamino]cyclobut-3-ene-1,2-dione were obtained. Yield=63%.

Workup

  1. customThe reaction medium was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washeluted with heptane/ethyl acetate at 4/1, 2:1

Sources & evidence

ORD record
ord-d946e9a49c784dabba03655778c14f15
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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