3-(4-Hydroxyphenyl)propionic acid → 2-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester

HRID 569938Notes

Reaction equation

HRID 569938 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C1N=CN(C(N2C=NC=C2)=O)C=1>CCN(CC)CC>[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH:19][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:15]

Participants

5

Reactant 3

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 682631,1'-CarbonyldiimidazoleHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 102641582-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (2.49 g, 15 mmol) was reacted with glycine ethyl ester hydrochloride in the presence of CDI and Et3N as described in Example 56 Part A. After removal of the solvent the residue was dissolved in CHCl3 and washed with 1N HCl, saturated NaHCO3 solution and saturated NaCl solution. After drying (MgSO4) and removal of the solvent in vacuo crude title ester remained (2.44 g) as a viscous oil. NMR indicated this contained a major impurity but it was used without further purification.

Workup

  1. customAfter removal of the solvent the residue
  2. dissolutionwas dissolved in CHCl3
  3. washwashed with 1N HCl, saturated NaHCO3 solution and saturated NaCl solution
  4. customAfter drying
  5. custom(MgSO4) and removal of the solvent in vacuo crude title ester
  6. customwas used without further purification

Sources & evidence

ORD record
ord-2f610ca1fde24011bcaed02150a9b629
Source dataset
uspto-grants-1988_03
Patent number
US04734424

Reaction notes

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