Sodium Hydroxide → (6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acid

HRID 2383313Notes

Reaction equation

HRID 2383313 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:35])[C:14]([C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH:30]([CH3:32])[CH3:31])=[C:25]([C:33]#[N:34])[CH:24]=4)[O:20][N:19]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])CCC.[OH-].[Na+]>C(O)C>[C:33]([C:25]1[CH:24]=[C:23]([C:21]2[O:20][N:19]=[C:18]([C:14]3[C:13]([CH3:35])=[C:12]4[C:17](=[CH:16][CH:15]=3)[CH:8]([CH2:7][C:6]([OH:43])=[O:5])[N:9]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:10][CH2:11]4)[N:22]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH:30]([CH3:31])[CH3:32])#[N:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 595910961,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 59591092(6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)acetic acidYield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1h)-isoquinolinecarboxylate (Preparation 21; 41 mg, 0.070 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (0.070 ml, 0.139 mmol) and the resulting mixture was stirred at room temperature for ca. 3.5 h. Most of the solvent was removed and the residue was partitioned between ether and water (with dropwise addition of 2N sodium hydroxide to keep the mixture basic). The layers were separated, and the aqueous layer acidified 2N aqueous hydrochloric acid giving a white precipitate which was extracted twice with ethyl acetate. The combined ethyl acetate fractions were dried over MgSO4 and concentrated in vacuo to give the title compound (38 mg).

Workup

  1. customMost of the solvent was removed
  2. customthe residue was partitioned between ether and water (
  3. additionwith dropwise addition of 2N sodium hydroxide
  4. customThe layers were separated
  5. extractionwas extracted twice with ethyl acetate
  6. dry with materialThe combined ethyl acetate fractions were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-790637ce38684c7bb734604e91dde6d6
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

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