Hydrochloric Acid → HCID 23168907, compound

HRID 1402927Notes

Reaction equation

HRID 1402927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[C:12]1([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 75190N-Phenylglycine ethyl esterHCID 906924-Chlorophenylacetyl chloride

Product 1

HCID 23168907HCID 23168907, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercial 4-chloro-phenylacetyl chloride (0.95 g) was added dropwise to a stirred solution of commercial ethyl N-phenylglycinate (1 g) and dry pyridine (3 ml) in dichloromethane (20 ml) under nitrogen atmosphere at rt. After stirring for 72 h the mixture was poured into 10% HCl solution and extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, dried over MgSO4, and concentrated. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 4:1) to give ethyl N-(4-chlorophenylacetyl)-N-phenylglycinate (0.95 g) as colourless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-f3574939412146a6a98e558775127ced
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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