Lithium Hydroxide → HCID 67194117, compound

HRID 2366961Notes

Reaction equation

HRID 2366961 reaction equation
[OH-].[Li+].[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[C@H:9]([NH:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:8][C@@H:7]1[CH3:36])(=[O:5])[CH3:4]>CO>[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[C@H:9]([NH:29][C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:8][C@@H:7]1[CH3:36])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67196970HCID 67196970, compound

Product 1

HCID 67194117HCID 67194117, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide (1N in water, 2 mL, 2.000 mmol) was added to a solution of ethyl 3-{4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}propanoate (for a preparation see Intermediate 101) (39.7 mg, 0.085 mmol) in methanol (5 mL). The reaction mixture was stirred at room temperature for 12 h then most of the solvent was removed in vacuo. The residue was partitioned between AcOEt (30 mL), water (20 mL) and glacial acetic acid (0.5 mL). The layers were separated and the organic layer was washed with brine (20 mL). The combined aqueous phases were extracted with AcOEt (20 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 3-{4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}propanoic acid (35.8 mg, 0.082 mmol, 96%) as a white solid.

Workup

  1. custommost of the solvent was removed in vacuo
  2. customThe residue was partitioned between AcOEt (30 mL), water (20 mL) and glacial acetic acid (0.5 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (20 mL)
  5. extractionThe combined aqueous phases were extracted with AcOEt (20 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb0129d28acc4b12a076accc2eeec0fd
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…