Potassium Hydroxide → 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid

HRID 1786049Notes

Reaction equation

HRID 1786049 reaction equation
[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2].[OH-].[K+]>O1CCCC1.CO>[C:1]([N:4]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]([C:17]2[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH:24]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[O:16])[C@@H:7]([CH3:36])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68920582methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate

Product 1

HCID 575955164-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydro-quinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoate was hydrolyzed to the acid by dissolving in 6 ml tetrahydrofuran/methanol (1/1) and potassium hydroxide (0.04 g in 2 ml water) was added. The mixture was heated to 50° C. for 18 hours. The mixture was cooled to room temperature and concentrated. Then neutralized with 1M HCl and extracted with dichloromethane. The dichloromethane solution was dried and concentrated. The residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol) to afford 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-2-(diethylamino)butanoic acid (0.04 g, 55%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane solution was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (87% CH2Cl2/13% methanol)

Sources & evidence

ORD record
ord-41a7afebb8de40dc819fe91dbbc286c1
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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