Glycine → HCID 59689159, compound

HRID 2425267Notes

Reaction equation

HRID 2425267 reaction equation
[OH-].[Na+].O.[NH2:4][CH2:5][C:6]([OH:8])=[O:7].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18](Cl)=[O:19])=[CH:12][CH:11]=1>O1CCOCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([NH:4][CH2:5][C:6]([OH:8])=[O:7])=[O:19])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 750GlycineHCID 962WaterHCID 14798Sodium HydroxideHCID 122065164-Chlorobenzenepropanoyl chloride

Product 1

HCID 59689159HCID 59689159, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 26 mmol sodium hydroxide in 7 ml water 8.7 mmol of glycine were added. The mixture was cooled in an ice-bath and a solution of 8.7 mmol 3-(4-chloro-phenyl)-propionyl chloride (CA [52085-96-8]) in 10 ml dioxane was slowly added over a period of 20 minutes. After stirring overnight at room temperature, the mixture was extracted with diethyl ether. The aqueous phase was acidified by addition of diluted hydrochloric acid and filtered. Trituration of the solid in diethyl ether yielded the title compound as a colorless solid. Yield=42%.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. extractionthe mixture was extracted with diethyl ether
  3. additionThe aqueous phase was acidified by addition of diluted hydrochloric acid
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a8054e4b041d4fe9b11a6fc23b929320
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

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