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

HRID 1626853Notes

Reaction equation

HRID 1626853 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-dee1e5316702402d92497bf85e318d48
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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