Water → Ethyl beta-[[2-[[(3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoate

HRID 378130

Reaction equation

HRID 378130 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7](C(=O)NCC(O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl.[NH2:19][CH:20]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[C:33]([O-:36])([O-])=O.[K+].[K+].O.[CH3:40][N:41]([CH:43]=[O:44])C>CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[CH:5]=[C:6]([C:43]([NH:41][CH2:40][C:33]([NH:19][CH:20]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:36])=[O:44])[CH:7]=[CH:15][CH:16]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 175494-Nitrohippuric acidHCID 22608516Ethyl 3-amino-3-(pyridin-3-yl)propanoate--hydrogen chloride (1/2)

Product 1

HCID 22608595Ethyl beta-[[2-[[(3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of p-nitrohippuric acid (5.6 g) in DMF (25 ml) was treated with DSC (9.6 g) and a catalytic amount of DMAP. After 5 hours, a solution of ethyl 3-amino-3-(3-pyridyl)propanoate 2HCl (8 g) and K2CO3 (2 g) in saturated aqueous NaHCO3 (25 ml) was added. The reaction mixture was stirred overnight at room temperature. H2O (25 ml) was added and the mixture was filtered. The resulting solid was washed with H2O (25 ml), slurried with CH3CN (25 ml) and filtered. Ethyl β-[[2-[[[3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoate (6.5 g) was obtained as a white solid. MS was consistent with the desired product.

Workup

  1. filtrationthe mixture was filtered
  2. washThe resulting solid was washed with H2O (25 ml)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0e0771c53c214db587efd5f6a1196709
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

Loading…