Sodium Hydroxide → (6-(5-{3-Chloro-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 2383312Notes

Reaction equation

HRID 2383312 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:34])[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]([Cl:33])[CH:24]=4)[O:20][N:19]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])CCC.[OH-].[Na+]>C(O)C>[Cl:33][C:25]1[CH:24]=[C:23]([C:21]2[O:20][N:19]=[C:18]([C:14]3[C:13]([CH3:34])=[C:12]4[C:17](=[CH:16][CH:15]=3)[CH:8]([CH2:7][C:6]([OH:42])=[O:5])[N:9]([C:35]([O:37][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:36])[CH2:10][CH2:11]4)[N:22]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH:30]([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 595910751,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 59591087(6-(5-{3-Chloro-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 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 20; 92 mg, 0.154 mmol) in ethanol (3 ml) was added sodium hydroxide (0.154 ml, 0.308 mmol) and the resulting mixture was stirred at room temperature for ca 3.5 h. Most of the solvent was removed and the residue 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 with 2N aqueous hydrochloric acid and extracted twice with ethyl acetate. The combined ethyl acetate fractions were dried over MgSO4 and concentrated in vacuo to give the title compound (75 mg) as a pale yellow oil.

Workup

  1. customMost of the solvent was removed
  2. customthe residue partitioned between ether and water (
  3. additionwith dropwise addition of 2N sodium hydroxide
  4. customThe layers were separated
  5. extractionextracted 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-0584bd419d54466d88aba8df756aae27
Source dataset
uspto-grants-2012_09
Patent number
US08263620B2

Reaction notes

Loading…