1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852518Notes

Reaction equation

HRID 852518 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:18]N(C)CCCN=C=NCC>CO.CCOCC.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=[C:2]([NH2:1])[CH:3]=1

Participants

6

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222529903-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid

Product 1

HCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl esterYield 68.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D6) (2.2 g, 10 mmol, 1 equiv) in MeOH/Et2O (1:1, 20 ml) was added 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (2.3 g, 12 mmol, 1.2 equiv), DMAP (112 mg, 1 mmol, 0.1 equiv) and the resulting mixture was stirred at room temperature for 16 h then diluted with AcOEt. The organic phase was washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give 3-amino-5-(2-oxo pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (1.6 g, 68%) as a white solid.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-694257ef59d945ae9973de5d1b43cade
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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