Lithium Hydroxide → 2-[6-(3-Fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic Acid

HRID 2415437Notes

Reaction equation

HRID 2415437 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:13]=2)[C:8]1=[O:26])[CH3:6])C.[OH-].[Li+]>O.O1CCCC1>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:26])[N:7]([CH:5]([CH3:6])[C:4]([OH:27])=[O:3])[CH2:16][CH2:15]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 690405202-[6-(3-Fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic Acid Ethyl Ester

Product 1

HCID 226419002-[6-(3-Fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the 2-[6-(3-fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid ethyl ester (0.087 g, 0.234 mmol) (example 2) and lithium hydroxide (0.0062 g, 0.258 mmol) in water and tetrahydrofuran (1:1 v:v, 9 mL) was stirred at room temperature for 2 h. The THF was evaporated and the mixture acidified to pH 3-4 with 0.1N HCl. After extraction with ethyl acetate, drying of the organic layer with MgSO4, filtration and evaporation a white solid was obtained (0.080 g, 99%). MS: m/e=342.1 (M−H+).

Workup

  1. customThe THF was evaporated
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialdrying of the organic layer with MgSO4, filtration and evaporation a white solid
  4. customwas obtained (0.080 g, 99%)

Sources & evidence

ORD record
ord-e3c400b01dc542b393ad399f8efa6717
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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