Sodium Hydroxide → N-[3-(3-Hydroxyphenyl)acryloyl]-O4-Methyl-L-Tyrosine

HRID 1746558Notes

Reaction equation

HRID 1746558 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]([NH:15][C@H:16]([C:26]([O:28]C)=[O:27])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:14])[CH:8]=[CH:9][CH:10]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]([NH:15][C@H:16]([C:26]([OH:28])=[O:27])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[O:14])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86655465HCID 86655465, compound

Product 1

HCID 86655504N-[3-(3-Hydroxyphenyl)acryloyl]-O4-Methyl-L-TyrosineYield 52.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol (240 mL) solution of the compound obtained in Example 36 (3.1 g) was added dropwise 1 mol/L of an aqueous sodium hydroxide solution (24 mL) at room temperature, and the mixture was allowed to stir for 17 hours. To the residue obtained by distilling off the solvent under a reduced pressure was added water, and the mixture was made acidic with dilute hydrochloric acid, and thereafter extracted with ethyl acetate. 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 (1.4 g, 51%) as an amorphous solid product.

Workup

  1. customTo the residue obtained
  2. distillationby distilling off the solvent under a reduced pressure
  3. additionwas added water
  4. extractionextracted 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-1d7e95d3ebbe45249102412f80c4d7b9
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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