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

HRID 1178069

Reaction equation

HRID 1178069 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([OH:21])=O)=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH2:50])[CH3:46]>CN(C=O)C.O>[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH:50][C:19](=[O:21])[CH2:18][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=1)[CH3:46]

Participants

8

Reactant 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 102641582-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl esterYield 130%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (390 mg, 0.52 mL, 3.02 mmol) was added to a stirred solution of 3-[4-hydroxy phenyl]propionic acid (100 mg, 0.60 mmol) in DMF (10 mL). HOBT (90 mg, 0.67 mmol) and EDCI.HCl (290 mg, 1.51 mmol) were added at room temperature. After 2 minutes glycine ethyl ester hydrochloride (100 mg, 0.72 mmol) was added. The resulting mixture was stirred at room temperature for 48 hours. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 196 mg of [3-(4-hydroxy-phenyl) propionylamino]-acetic acid ethyl ester. 1H NMR (CDCL3): δ 7 (d, 2H), 6.65 (d, 2H), 6.0 (bs, 1H), 4.15 (q, 2H), 4.0 (d, 2H), 3.5 (s, 2H), 2.8 (t, 2H), 2.45 (t, 2H), 1.2 (t, 3H), LC-MS purity: 68.23%.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d37264a6fbb144a8a5e7942dea211699
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

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