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

HRID 49542Notes

Reaction equation

HRID 49542 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].ClCCl.CN([CH:18]=[O:19])C.C([N:23](C(C)C)CC)(C)C.[CH2:29]1C[O:32][CH2:31][CH2:30]1>>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:23][CH2:29][CH2:30][C:31]([O:19][CH3:18])=[O:32])=[O:9])=[CH:10][CH:11]=1)=[O:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 120884-Formylbenzoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 161003253-(4-Formylbenzoylamino)propionic acid methyl ester

Procedure

To a solution of the 4-formylbenzoic acid in a suitable solvent such as dichloromethane, DMF or THF was added diisopropylethylamine (3 eq) and 3-[(dimethyliminium)-(dimethylamino)methyl]-1,2,3-benzotriazol-1-ium-1-olate hexafluorophosphate (HBTU) (1.1 eq). The reaction was allowed to stir for 30 min before ethyl or methyl-3-aminopropionate hydrochloride (1.1 eq) was added. The solution was stirred at room temperature for 4 hours. The solvents were evaporated under reduced pressure. The residue was taken up in ethyl acetate and 1N hydrochloric acid. The organic layer was separated and washed with water (2×), aqueous sodium hydrogen carbonate (3×), brine (2×), dried over magnesium sulphate and concentrated to give the desired product.

Workup

  1. additionwas added
  2. customThe solvents were evaporated under reduced pressure
  3. customThe organic layer was separated
  4. washwashed with water (2×), aqueous sodium hydrogen carbonate (3×), brine (2×)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b998d2a1129e49029b50fcc8e136bfae
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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