HCID 68815188, compound → HCID 68814256, compound

HRID 1436668Notes

Reaction equation

HRID 1436668 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:17]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C>[OH-].[Li+].C1COCC1.O>[CH:19]([O:18][C:16]1[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=1)[C:4]([OH:22])=[O:3])([CH3:21])[CH3:20]

Participants

5

Reactant 1

HCID 68815188HCID 68815188, compound

Product 1

HCID 68814256HCID 68814256, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve crude 5-isopropoxy-N-methyl-N-propyl-isophthalamic acid ethyl ester (12.7 mmol) in 1 N lithium hydroxide (50 mL) and THF (50 mL). Stir at room temperature for 4 h. Dilute with water (100 mL). Wash with diethyl ether (3×30 mL), and acidify the aqueous layer with 5 N HCl to about pH=1. Extract with ethyl acetate to give the title compound (3.1 g, 87% over 2 steps).

Workup

  1. washWash with diethyl ether (3×30 mL)
  2. extractionExtract with ethyl acetate

Sources & evidence

ORD record
ord-f78bb0d35250471385e099b408c031a9
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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