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

HRID 2059951Notes

Reaction equation

HRID 2059951 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:17]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[C:24]([Cl:32])[CH:23]=4)[O:19][N:18]=3)[C:12]=2[CH3:16])[CH2:7]1)C.[OH-].[Na+]>C(O)C.C1COCC1>[Cl:32][C:24]1[CH:23]=[C:22]([C:20]2[O:19][N:18]=[C:17]([C:11]3[C:12]([CH3:16])=[C:13]4[C:8](=[CH:9][CH:10]=3)[CH2:7][N:6]([CH2:5][C:4]([OH:33])=[O:3])[CH2:15][CH2:14]4)[N:21]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH:29]([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59370488ethyl[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetate

Product 1

HCID 57505835[6-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl]acetate (Preparation 21; 75 mg; 0.16 mmol) in ethanol (2 ml) and THF (2 ml) at room temperature was added 2N sodium hydroxide, and the resulting mixture was stirred at room temperature for 40 min. The solvents were removed and the residue dissolved in water (ca. 1 ml). Acetic acid (1 ml) was added, all solvents were removed and the residue co-evaporated with toluene to give a pale yellow solid. This solid was triturated with diethyl ether to give the title compound, which was filtered off as a pale yellow solid (50 mg).

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue dissolved in water (ca. 1 ml)
  3. additionAcetic acid (1 ml) was added
  4. customall solvents were removed
  5. customthe residue co-evaporated with toluene to give a pale yellow solid
  6. customThis solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-73b6acda464d4549898fb4c9d2ba0db3
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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