Sodium Bicarbonate → HCID 68295786, compound

HRID 572475Notes

Reaction equation

HRID 572475 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:6]1[N:7]([CH3:25])[C:8](=[O:24])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:5].C([O-])(O)=O.[Na+]>C(OC(C)=O)(C)(C)C>[CH3:1][O:2][C:3](=[O:26])[CH:4]([O:5][C:9]([CH3:14])([CH3:10])[CH3:8])[C:6]1[N:7]([CH3:25])[C:8](=[O:24])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68295008HCID 68295008, compound

Product 1

HCID 68295786HCID 68295786, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of [4-(3,4-Difluoro-phenyl)-2-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl]-hydroxy-acetic acid methyl ester (114 mg, 0.31 mmol) in t-BuOAc (10 ml) was added HClO4 (0.17 ml, 1.11 mmol). The reaction mixture was stirred at RT overnight. TLC showed most SM consumed, ended the reaction, added ice-water, adjusted to pH=6 by adding 1N aq NaHCO3, extracted with EA, washed with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by pre-TLC to afford title product. (m=57 mg, yield=43.2%).

Workup

  1. customconsumed
  2. customthe reaction
  3. extractionextracted with EA
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by pre-TLC

Sources & evidence

ORD record
ord-e2feb51db4364c22917ae767a00a3f6f
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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