Potassium Hydroxide → HCID 18767755, compound

HRID 480139Notes

Reaction equation

HRID 480139 reaction equation
C[O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13](=O)[N:14]([C:22]3[C:23](=[O:36])[N:24]([CH2:33][CH2:34][CH3:35])[C:25](=[O:32])[N:26]([CH2:29][CH2:30][CH3:31])[C:27]=3[NH2:28])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].[OH-].[K+]>CC(O)C.O>[CH2:15]([N:14]1[C:22]2[C:23](=[O:36])[N:24]([CH2:33][CH2:34][CH3:35])[C:25](=[O:32])[N:26]([CH2:29][CH2:30][CH3:31])[C:27]=2[N:28]=[C:13]1[C:8]12[CH2:7][CH2:6][C:5]([C:3]([OH:2])=[O:4])([CH2:12][CH2:11]1)[CH2:10][CH2:9]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67078826HCID 67078826, compound

Product 1

HCID 18767755HCID 18767755, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 4-[(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-benzyl-carbamoyl]-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (430 mg, 0.843 mmol) in i-PrOH (20 ml) was added 2 N KOH (4.0 eq, 3.37 mmol, 1.7 ml) and the resulting mixture was heated at reflux for 26 h. The cool reaction mixture was concentrated in vacuo to give a semi-solid residue that was diluted with water and extracted with CHCl3. The aqueous phase was acidified with concentrated HCl to afford a white precipitate that was collected and dried (381 mg, 91%). MS: 479 (MH+).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 26 h
  3. customThe cool reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customto give a semi-solid residue that
  6. extractionextracted with CHCl3
  7. customto afford a white precipitate that
  8. customwas collected
  9. customdried (381 mg, 91%)

Sources & evidence

ORD record
ord-ece1a03ae3c448c0945ae1de43299058
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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