Lithium Hydroxide → 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acid

HRID 2366959Notes

Reaction equation

HRID 2366959 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][C:23]([O:25]CC)=[O:24])=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[C@H:9]([NH:28][C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:8][C@@H:7]1[CH3:35])(=[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][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[C@H:9]([NH:28][C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:8][C@@H:7]1[CH3:35])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68185396ethyl 2-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetate

Product 1

HCID 529352352-(4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)phenyl)acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide (4N in water, 1 mL, 4.00 mmol) was added to a solution of ethyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetate (for a preparation see Intermediate 100) (32.6 mg, 0.072 mmol) in methanol (3 mL). The resulting mixture was stirred under nitrogen at room temperature for 12 h then most of the solvent was removed in vacuo. The residue was partitioned between AcOEt (30 mL) and water (15 mL) and the layers were separated. The aqueous phase was extracted with AcOEt (15 mL). The combined organic phases were washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo. Purification of the residue by MDAP (modifier: formic acid) gave {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetic acid (23.8 mg, 0.056 mmol, 78%) as a white solid.

Workup

  1. custommost of the solvent was removed in vacuo
  2. customThe residue was partitioned between AcOEt (30 mL) and water (15 mL)
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with AcOEt (15 mL)
  5. washThe combined organic phases were washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by MDAP (modifier: formic acid)

Sources & evidence

ORD record
ord-9f6b5c1fc80d49928847ac99283cf7d4
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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