Methanol → HCID 57763473, compound

HRID 230818Notes

Reaction equation

HRID 230818 reaction equation
[CH2:1]([C:3]([C:21]1[CH:34]=[CH:33][C:24]([C:25]([NH:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:26])=[C:23]([CH3:35])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].CO.[OH-].[Na+]>O>[CH2:1]([C:3]([C:21]1[CH:34]=[CH:33][C:24]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[C:23]([CH3:35])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86604781HCID 86604781, compound

Product 1

HCID 57763473HCID 57763473, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl (4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]propyl}-2-methylbenzoylamino)acetate (0.43 g, 0.89 mmol), CH3OH (10 ml), NaOH (0.18 g, 4.46 mmol), and H2O (1 mL) is refluxed for 2 h. The reaction is concentrated, diluted with H2O (5 ml), acidified (pH 3-4) with 0.1 M HCl and extracted with EtOAc (3×15 mL). The combined organic layers are MgSO4 dried, and concentrated to give the title compound (0.29 g, 71%).

Workup

  1. temperatureis refluxed for 2 h
  2. concentrationThe reaction is concentrated
  3. additiondiluted with H2O (5 ml)
  4. extractionextracted with EtOAc (3×15 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-14fbd3225ed7449e9d4a57bdd81a5500
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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