Sodium Hydroxide → 3-[6-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoic acid

HRID 2059950Notes

Reaction equation

HRID 2059950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([CH3:34])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH2:23][N:22]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH2:21][CH2:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([CH3:34])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH2:23][N:22]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:21][CH2:20]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59370484Ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate

Product 1

HCID 441250323-[6-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]propanoate (Preparation 20; 90 mg; 0.186 mmol) in ethanol (2 ml) and THF (2 ml) at room temperature was added 2N sodium hydroxide (0.186 ml; 0.372 mmol), and the resulting mixture was stirred at room temperature for ca. 2.5 h. Removal of most of the solvents, dilution with ca. 1 ml of water, followed by addition of acetic acid (ca. 300 μl) gave a precipitate. The mixture was extracted with dichloromethane to give, after removal of the solvent and trituration with diethyl ether, the title compound as a white solid (40 mg).

Workup

  1. customRemoval of most of the solvents, dilution with ca. 1 ml of water
  2. additionfollowed by addition of acetic acid (ca. 300 μl)
  3. customgave a precipitate
  4. extractionThe mixture was extracted with dichloromethane
  5. customto give
  6. customafter removal of the solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-cb32ddd632c946cfb91e1f9fe52ce198
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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