Sodium Hydroxide → HCID 86655519, compound

HRID 1746577Notes

Reaction equation

HRID 1746577 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([NH:12][C@H:13]([C:25]([O:27]C)=[O:26])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:11].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([NH:12][C@H:13]([C:25]([OH:27])=[O:26])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86655520HCID 86655520, compound

Product 1

HCID 86655519HCID 86655519, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol (260 mL) of the compound obtained in Example 57 (6.9 g) was added dropwise 1 mol/L of an aqueous sodium hydroxide solution (26 mL) at room temperature, and the mixture was allowed to stir for 21 hours. To the residue obtained by distilling off the solvent under a reduced pressure was added water, and the mixture was made acidic with 10% citric acid. The solution was extracted with ethyl acetate and thereafter the organic layer was washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, to give the captioned compound (5.4 g, 81%) as an oily product.

Workup

  1. customTo the residue obtained
  2. distillationby distilling off the solvent under a reduced pressure
  3. additionwas added water
  4. extractionThe solution was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-2de306c7b43944b28cc146968874bf3f
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…