3-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide → 2-hydroxy-N,N-dimethyl-3-(2-{[(R)-(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamide

HRID 1528211Notes

Reaction equation

HRID 1528211 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C@H:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:16][C:17]1[C:20](=[O:21])[C:19](=O)[C:18]=1[NH:23][C:24]1[C:25]([OH:35])=[C:26]([CH:32]=[CH:33][CH:34]=1)[C:27]([N:29]([CH3:31])[CH3:30])=[O:28])C>CO>[OH:35][C:25]1[C:24]([NH:23][C:18]2[C:17](=[O:16])[C:20](=[O:21])[C:19]=2[NH:13][C@@H:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:8]2([CH3:12])[CH2:9][O:10][CH2:11]2)=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([N:29]([CH3:31])[CH3:30])=[O:28]

Participants

4

Reactant 2

HCID 118554143-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamideHCID 89525580C-(R)-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine

Product 1

HCID 715259742-hydroxy-N,N-dimethyl-3-(2-{[(R)-(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamideYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

471 mg (2.6 mmol, 1.3 eq) of C—(R)-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine were added to 609 mg (2.0 mmol, 1 eq) of 3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-N,N-dimethylbenzamide dissolved under hot conditions in 40 ml of methanol. The reaction medium was heated at 50° C. for 17 hours. The methanol was evaporated off and the residue (green oil) was chromatographed on silica gel (column puriFlash IR-50SI-80G, Spot II) eluted with dichloromethane/methanol (97/3). The amorphous solid was taken up with diethyl ether to give a yellow powder which was recrystallized from n-propanol. 519 mg of 2-hydroxy-N,N-dimethyl-3-(2-{[(R)-(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut-1-enylamino)benzamide were obtained. Yield=70%.

Workup

  1. customThe methanol was evaporated off
  2. customthe residue (green oil) was chromatographed on silica gel (column puriFlash IR-50SI-80G, Spot II)
  3. washeluted with dichloromethane/methanol (97/3)
  4. customto give a yellow powder which
  5. customwas recrystallized from n-propanol

Sources & evidence

ORD record
ord-b96494cd7958406cb29b6b6e06e8db07
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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