Sodium Hydroxide → HCID 59218425, compound

HRID 2246669Notes

Reaction equation

HRID 2246669 reaction equation
[CH3:1][C:2]([CH3:32])=[CH:3][C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=3[CH:19]=2)=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8]C)=[O:7].[OH-].[Na+]>O.CCO>[CH3:1][C:2]([CH3:32])=[CH:3][C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=3[CH:19]=2)=[CH:12][CH:11]=1)[CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59218478HCID 59218478, compound

Product 1

HCID 59218425HCID 59218425, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of compound 33.2 (0.15 mmol) and sodium hydroxide (0.8 mmol) in water (1 mL) and EtOH (3 mL) is stirred at room temperature overnight. EtOH is removed under reduced pressure, and the remaining solution acidified with 1N HCl to pH 3-5 and then diluted with EtOAc (70 mL), washed with saturated brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and purified by column chromatography (silica gel; 1:9 MeOH/DCM) to yield compound 33.

Workup

  1. customEtOH is removed under reduced pressure
  2. additiondiluted with EtOAc (70 mL)
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography (silica gel; 1:9 MeOH/DCM)

Sources & evidence

ORD record
ord-3f997f9a0766435d8bce478a918bdaef
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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