Sodium Hydroxide → HCID 68580202, compound

HRID 644377Notes

Reaction equation

HRID 644377 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:35])[CH2:21][CH2:20]2)=[O:18])[C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[CH2:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:35])[CH2:21][CH2:20]2)=[O:18])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68579013ethyl 3-(3,4-dimethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionate

Product 1

HCID 68580202HCID 68580202, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17.5 g (36.6 mmol) ethyl 3-(3,4-dimethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionate dissolved in 100 mL MeOH was combined with 200 mL 1 M NaOH and stirred overnight at RT. The reaction mixture was filtered, the filtrate washed three times with tert-butylmethylether and combined with 200 mL 1 M HCl. The aqueous phase was extracted three times with EtOAc, the combined organic phases were dried, filtered and evaporated down under reduced pressure. The residue was triturated with diisopropylether, suction filtered, stirred with diethyl ether and dried at 50° C. in the circulating air dryer.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate washed three times with tert-butylmethylether
  3. extractionThe aqueous phase was extracted three times with EtOAc
  4. customthe combined organic phases were dried
  5. filtrationfiltered
  6. customevaporated down under reduced pressure
  7. customThe residue was triturated with diisopropylether, suction
  8. filtrationfiltered
  9. stirringstirred with diethyl ether
  10. customdried at 50° C. in the circulating air dryer

Sources & evidence

ORD record
ord-1c0bd74828c24965ad0d5389e01cebec
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

Loading…