Water → Ethyl 2-(3-(2-chloroacetamido)-4-hydroxyphenyl)propanoate

HRID 660293Notes

Reaction equation

HRID 660293 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Cl:16][CH2:17][C:18](Cl)=[O:19].O>CC(C)CC(=O)C>[Cl:16][CH2:17][C:18]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 12202638Ethyl 3-amino-4-hydroxy-phenyl-propionate

Product 1

HCID 57742174Ethyl 2-(3-(2-chloroacetamido)-4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-(3-amino-4-hydroxyphenyl)propanoate (104 mg, 0.497 mmol) in 4-methyl-2-pentanone (4 mL) was added chloroacetylchloride (56 mg, 0.496 mmol) at room temperature and stirred for 20 hours at 80° C. The reaction mixture was cooled to room temperature and added water (30 mL). The mixture was extracted with EtOAc. The organic layer was dried with MgSO4 and filtered. EtOAc was removed by evaporation. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=2/1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customEtOAc was removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=2/1

Sources & evidence

ORD record
ord-128f3085048a4dd5b1d5ff29cc26b51d
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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