Lithium Hydroxide → HCID 60141952, compound

HRID 572471Notes

Reaction equation

HRID 572471 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5]1[N:6]([CH3:26])[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH3:23])=[C:17]([CH3:24])[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[Li+].[OH-]>C1COCC1>[C:28]([O:27][CH:4]([C:5]1[N:6]([CH3:26])[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH3:23])=[C:17]([CH3:24])[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]([OH:32])=[O:2])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68294963HCID 68294963, compound

Product 1

HCID 60141952HCID 60141952, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-Butoxy-[4-(4-methoxy-3,5-dimethyl-phenyl)-2-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester (130 mg, 0.3 mmol) in THF (3.0 ml) was added an aqueous LiOH (1N, 1.22 ml). The mixture was stirred at 60° C. overnight. LCMS showed SM was consumed, cooled to RT, removed the solvent, added water, extracted with EA to remove impurity, the aqueous layer was adjusted to pH=6 with 1N HCl, extracted with EA, the organic layer was washed with water and brine, dried over Na2SO4, filtered, concentrated to dryness, gave the desired product. (m=73 mg, Yield: 58%): 1HNMR: (400 MHz, d6-DMSO) δ 1.03 (s, 9H), 2.31 (s, 6H), 3.64 (s, 3H), 3.79 (s, 3H), 5.29 (s, 3H), 6.94 (s, 1H), 7.13 (d, J=8.0 Hz, 1H), 7.24 (s, 1H), 7.49 (m, 2H), 8.46 (d, J=8.0 Hz, 1H). LCMS: (10-80 AB—2MIN-E.M): Rt=1.258, purity=96.0%, M+1=424.

Workup

  1. customwas consumed
  2. temperaturecooled to RT
  3. customremoved the solvent
  4. additionadded water
  5. extractionextracted with EA
  6. customto remove impurity
  7. extractionextracted with EA
  8. washthe organic layer was washed with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-87364aebb35343f18f9ca3f24d8d4fe3
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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