Benzoic Acid → Ethyl Hippurate

HRID 1178077Notes

Reaction equation

HRID 1178077 reaction equation
CCN([CH:7]([CH3:9])C)C(C)C.[C:10]([OH:18])(=[O:17])[C:11]1C=CC=CC=1.[CH:19]1[CH:20]=[CH:21][C:22]2N(O)N=N[C:23]=2[CH:24]=1.CCN=C=NCCCN(C)C.Cl.C[N:42]([CH:44]=[O:45])C>O>[CH2:7]([O:18][C:10](=[O:17])[CH2:11][NH:42][C:44](=[O:45])[C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:24]=1)[CH3:9]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 226558Ethyl HippurateYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (0.425 mL, 2.46 mmol) was added to a stirred solution of benzoic acid (100 mg, 0.82 mmol) in DMF (2 mL). HOBT (132 mg, 0.98 mmol) and EDCI.HCl (188 mg, 0.98) were then added, followed by the addition of ethyl glycine ester hydrochloride (0.82 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. 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 the crude product. Purification using column chromatography (using silica gel, 60-120 A° and 20% methanol in chloroform as the eluent) afforded Benzoylamino-acetic acid ethyl ester in 53% yield, LC-MS purity: 98%

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
  5. customto afford the crude product
  6. customPurification

Sources & evidence

ORD record
ord-003e4781e2da4c7097e39bb56d63f166
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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