Nicotinic Acid → 2-Benzoyl amino-pentane dioic acid dimethyl ester

HRID 82482Notes

Reaction equation

HRID 82482 reaction equation
[CH:1]1[CH:6]=N[CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.[CH3:10]N1CCOCC1.CCN=C=NCCCN(C)C.Cl.[CH3:29][O:30][C:31](=[O:40])[C@H:32]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[NH2:33]>C(Cl)Cl>[CH3:29][O:30][C:31](=[O:40])[C:32]([NH2:33])([C:7](=[O:9])[C:3]1[CH:2]=[CH:1][CH:6]=[CH:10][CH:4]=1)[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37]

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 79724-MethylmorpholineHCID 93032Dimethyl glutamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 866749232-Benzoyl amino-pentane dioic acid dimethyl esterYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of niacin (1.4 g, 11.42 mmol) in DCM (20 mL) were added N-methyl morpholine (3.76 mL, 34.2 mmol), EDCI.HCl (4.36 g, 34.2 mmol) and L-glutamic acid dimethyl ester (2.0 g, 11.42 mmol). The mixture was allowed to stir at room temperature (25° C.) over 3 h under nitrogen atmosphere. The resulting mixture was diluted with DCM (100 mL), washed with water (3×50 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was further purified by silica gel column chromatography to obtain required product as pale yellow oil (3.1 g, 73%).

Workup

  1. washwashed with water (3×50 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained upon evaporation of the solvent
  4. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-466ad572ab5643d8b303080aa2f9a680
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

Loading…