Methanol → HCID 28202523, compound

HRID 1746620Notes

Reaction equation

HRID 1746620 reaction equation
CO.[C:3]([NH:8][C@H:9]([C:20]([O:22]C)=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:7])/[CH:4]=[CH:5]/[CH3:6].[OH-].[Na+]>O>[C:3]([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:7])/[CH:4]=[CH:5]/[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67130832HCID 67130832, compound

Product 1

HCID 28202523HCID 28202523, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methanol (230 mL) solution of the compound obtained in Example 161 (4.4 g) was added 1 mol/L of an aqueous sodium hydroxide solution (23 mL), and the mixture was allowed to stir for 20 hours. Water was added to the residue obtained by distilling off the solvent under a reduced pressure, and the mixture was made acidic with a 10% aqueous citric acid solution. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated sodium chloride solution, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure, to give the captioned compound (3.0 g, 71%) as an amorphous solid product.

Workup

  1. customobtained
  2. distillationby distilling off the solvent under a reduced pressure
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-66a2e75f385342d9bf8f42df93aa7e65
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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