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

HRID 2366931Notes

Reaction equation

HRID 2366931 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]CC)=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:6][C@@H:5]1[CH3:33])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 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 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

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 61) (270 mg, 0.597 mmol) in methanol (6 mL) and water (2 mL) at room temperature was added sodium hydroxide (2N in water, 0.597 mL, 1.193 mmol) and the resulting mixture was stirred at this temperature for 6 h. 0.5 ml of 2N sodium hydroxide in water were then added and the resulting mixture was left standing for 16 h. Most of the methanol was then removed in vacuo and the residue was partitioned between water and Et2O. The layers were separated. The aqueous layer was acidified with 2 mL of 2N HCl in water and extracted twice with AcOEt. The combined AcOEt fractions were dried over MgSO4 and concentrated in vacuo to give {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}acetic acid (200 mg, 0.471 mmol, 79% yield) as a brown foam.

Workup

  1. waitthe resulting mixture was left
  2. waitstanding for 16 h
  3. customMost of the methanol was then removed in vacuo
  4. customthe residue was partitioned between water and Et2O
  5. customThe layers were separated
  6. extractionextracted twice with AcOEt
  7. dry with materialThe combined AcOEt fractions were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e654c3e33294426a9da1be3c284c70a
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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