Lithium Hydroxide → HCID 178518591, compound

HRID 538033Notes

Reaction equation

HRID 538033 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:23])[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-]>C1COCC1.O>[O:23]=[C:13]1[N:12]([CH2:11][C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178501110HCID 178501110, compound

Product 1

HCID 178518591HCID 178518591, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of trans-4-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexanecarboxylic acid methyl ester (15 g, 51.7 mmol) in a mixture of THF (240 mL) and H2O (60 mL), LiOH was added and the reaction was heated at 85° C. for 16 hours. The mixture was allowed to cool down to room temperature and the solvent removed under reduced pressure. The residue was dissolved in 100 mL of H2O and the solution acidified to pH 3. The precipitate formed was filtered and washed with 100 mL of CH3CN. The titled compound (11.9 g, 79%) was obtained as a white solid.

Workup

  1. additionwas added
  2. temperatureto cool down to room temperature
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was dissolved in 100 mL of H2O
  5. customThe precipitate formed
  6. filtrationwas filtered
  7. washwashed with 100 mL of CH3CN

Sources & evidence

ORD record
ord-650ed288b68d421cb317475f9b150f1f
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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