Hydrochloric Acid → HCID 28765045, compound

HRID 1402928Notes

Reaction equation

HRID 1402928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][C:13]([O:15]CC)=[O:14])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23168907HCID 23168907, compound

Product 1

HCID 28765045HCID 28765045, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl N-(4-chloro-phenylacetyl)-N-phenylglycinate (0.4 g) and 5M NaOH (2.4 ml) in EtOH (12 ml) was refluxed for 2 h. After cooling to rt the mixture was poured into water (30 ml), acidified to pH 2 with 10% HCl and extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with brine (20 ml), dried over MgSO4, and evaporated. The crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 3:2+3% formic acid) to afford N-((4-chlorophenylacetyl)-N-phenylglycine (0.1 g) as colourless solid.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 3:2+3% formic acid)

Sources & evidence

ORD record
ord-44b04ba5a7b14e2092114e22a13090fd
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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