Methanol → N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valine

HRID 606428Notes

Reaction equation

HRID 606428 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36]([O:38]C)=[O:37])[CH:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1.CO.O.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36]([OH:38])=[O:37])[CH:33]([CH3:35])[CH3:34])(=[O:29])=[O:30])=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 136380956methyl N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valinate

Product 1

HCID 136380958N-{[3'-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of methyl N-{[3′-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)biphenyl-4-yl]sulfonyl}valinate obtained in Reference Example 95 (0.250 g, 0.456 mmol) in THF (3 mL)-methanol (3 mL)-water (3 mL) was added 4N aqueous sodium hydroxide solution (0.399 mL, 1.60 mmol) at room temperature, and the mixture was stirred under heating at 80° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure, and the residue was diluted with water. The mixture was acidified with 1N hydrochloric acid, and partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol to give the title compound as a white powder (0.202 g, 83%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. custompartitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-d20f1c67d5b64deb9eece31ac70cb754
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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