Tetrahydrofuran → HCID 53817402, compound

HRID 1457986Notes

Reaction equation

HRID 1457986 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=[O:17].[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>>[C:1]([O:5][C:6]([NH:8][C:9]1([C:13](=[O:15])[CH2:29][C:30]([O:31][CH2:32][CH3:28])=[O:17])[CH2:10][CH2:11][CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-

Product 1

HCID 53817402HCID 53817402, compound

Procedure

To a 100.0 ml portion of ethanol were added 5.0 g (0.21 mmol) of magnesium and 15.0 ml of carbon tetrachloride in that order, followed by 1 hour of stirring at room temperature. Thereto was added dropwise ethyl hydrogen malonate. After 1 hour of stirring at room temperature, the solvent was evaporated to yield magnesium malonate as a colorless foamy substance. Separately, 55.29 g (0.26 mmol) of 1-tert-butoxycarbonylaminocyclobutanecarboxylic acid was dissolved in 450.0 ml of THF, mixed with 45.81 g (0.28 mmol) of 1,1'-carbonyldiimidazole and then stirred at room temperature for 1.5 hours. To this was added dropwise 450.0 ml of THF solution of the above magnesium salt in 30 minutes, followed by 2 days of stirring at room temperature. After evaporation of the solvent, the resulting residue was distributed between 10% citric acid aqueous solution and ethyl acetate. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent, the title compound was obtained quantitatively.

Workup

  1. waitfollowed by 2 days
  2. stirringof stirring at room temperature
  3. customAfter evaporation of the solvent
  4. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customBy evaporating the solvent

Sources & evidence

ORD record
ord-4eeb9f08c2f3428ba942078572c3d8dc
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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