Potassium Hydroxide → HCID 58134783, compound

HRID 444785Notes

Reaction equation

HRID 444785 reaction equation
[OH-].[K+].[C:3]([NH:11][C:12]1([CH2:16][C:17]([O:19]CC)=[O:18])[CH2:15][CH2:14][CH2:13]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCO>[C:3]([NH:11][C:12]1([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][CH2:14][CH2:13]1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58134741HCID 58134741, compound

Product 1

HCID 58134783HCID 58134783, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3N KOH (10 mL, 30 mmol) was added to a solution of ethyl 1-(benzoylamino)-cyclobutylacetate (3.87 g, 14.8 mmol) in EtOH (30 mL) at room temperature and the mixture was stirred for 1 hour. The reaction mixture was concentrated in vacuo and 6N HCl (5.0 mL) was added. The resulting precipitate was collected by filtration, washed successively with water and diisopropylether and dried to give the title compound (3.15 g, 91%) as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ 1.76-1.89 (2H, m), 2.16-2.26 (2H, m), 2.28-2.40 (2H, m), 2.90 (2H, s), 7.43 (2H, t, J=6.7 Hz), 7.50 (1H, t, J=6.7 Hz), 7.83 (2H, d, J=6.7 Hz), 8.45 (1H, s), 12.00 (1H, brs).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and 6N HCl (5.0 mL)
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed successively with water and diisopropylether
  5. customdried

Sources & evidence

ORD record
ord-b9de0520421542868041c262c420fe27
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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