4-Formylbenzoic acid → 3-(4-Formylbenzoylamino)propionic acid methyl ester

HRID 1633953Notes

Reaction equation

HRID 1633953 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH2:40]>CN(C=O)C.C(N(CC)CC)C>[CH3:35][O:36][C:37](=[O:41])[CH2:38][CH2:39][NH:40][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 120884-Formylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734767Methyl 3-aminopropanoate hydrochloride2×

Product 1

HCID 161003253-(4-Formylbenzoylamino)propionic acid methyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

4-Formylbenzoic acid (15 g, 100 mmol) was dissolved in DMF (250 mL) and 1-hydroxybenzotriazole (14.9 g, 110 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (21.1 g, 110 mmol) were added and the resulting mixture was stirred at room temperature for 30 minutes. Triethylamine (34.8 mL, 250 mmol) and β-alanine methyl ester hydrochloride (15.4 g, 110 mmol) were added and the resulting mixture was stirred at room temperature for 1 hour. More triethylamine (17.4 mL) and β-alanine methyl ester hydrochloride (7.7 g) were added and the mixture was stirred at room temperature for 16 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic phase was dried (MgSO4) and concentrated to afford 16.2 g (70%) of 3-(4-formylbenzoylamino)propionic acid methyl ester as an oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. stirringthe mixture was stirred at room temperature for 16 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bff5b7085eba48358b7e3ce8e2ebb6b9
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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