Water → HCID 57535885, compound

HRID 1455783Notes

Reaction equation

HRID 1455783 reaction equation
C([O:9][CH2:10][CH:11]([NH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=2)=[CH:17][C:16]=1[Cl:36])(=O)C1C=CC=CC=1.[OH-].[Na+].O>C(O)C>[CH2:29]([O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH:11]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:10][OH:9])=[C:16]([Cl:36])[CH:17]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23078153HCID 23078153, compound

Product 1

HCID 57535885HCID 57535885, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 128-2 (560 mg) was dissolved in ethanol (10 mL). To this solution, a 1 mol/L aqueous solution of sodium hydroxide (5 mL) was added and the mixture was stirred at room temperature for 1 hour. Following addition of water, the mixture was extracted with ethyl acetate and the extract was washed with a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous sodium sulfate. The solvent was concentrated and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product as a colorless oil (290 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  4. concentrationThe solvent was concentrated
  5. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c0498cc516114f659b0709caf4fe505e
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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