Sodium Hydroxide → HCID 67165334, compound

HRID 553018Notes

Reaction equation

HRID 553018 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:40][CH3:41])[C:9]([C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][C:32]([CH3:38])([CH3:37])[C:33]([O:35]C)=[O:34])=[CH:25][CH:24]=3)=[O:22])[C@@H:13]([CH3:39])[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C1COCC1.CO.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:40][CH3:41])[C:9]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]([C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][CH2:31][C:32]([CH3:37])([CH3:38])[C:33]([OH:35])=[O:34])=[CH:27][CH:28]=3)=[O:22])[CH:13]([CH3:39])[CH2:12]2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 131728940HCID 131728940, compound

Product 1

HCID 67165334HCID 67165334, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (±)-trans-methyl 5-(4-{[4-{[(4-chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (500 mg, 0.87 mmol) in 1:1 THF/methanol (5.0 mL) was added a solution of sodium hydroxide (69.5 mg, 1.74 mmol) in water (1.0 mL). The resulting mixture was heated at 60° C. for 18-20 hours and concentrated. The resulting residue was dissolved in water (˜50 mL), cooled to 0° C., and the solution acidified using 3N hydrochloric acid. The resulting precipitated material was collected via suction filtration, washed with 1N hydrochloric acid (3×25 mL), and dried to afford crude 5-(4-{[4-{[(4-Chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid as a mixture of cis and trans isomers. Purification via HPLC yielded (±)-trans-5-(4-{[4-{[(4-Chlorophenyl)(ethyl)amino]carbonyl}-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoic acid (23%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in water (˜50 mL)
  3. temperaturecooled to 0° C.
  4. customThe resulting precipitated material
  5. filtrationwas collected via suction filtration
  6. washwashed with 1N hydrochloric acid (3×25 mL)
  7. customdried

Sources & evidence

ORD record
ord-9384d59ea3bf40cfa9335d79b15c7e3f
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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