Nicotinic Acid → Glycine, N-(3-pyridinylcarbonyl)-, methyl ester

HRID 1650701Notes

Reaction equation

HRID 1650701 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.Cl.[NH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C1(N=C=NC2CCCCC2)CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1.O>[CH3:16][O:15][C:13]([CH2:12][NH:11][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)=[O:14]

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 521804Glycine, N-(3-pyridinylcarbonyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 50.0 g (0.400 mol) of nicotinic acid, 50.0 g (0.400 mol) of methyl glycinate hydrochloride, 90 g (0.440 mol) of dicyclohexylcarbodiimide, and 2 g of p-toluenesulfonic acid in 500 ml of dry pyridine was stirred overnight at room temperature. Filtration and evaporation in vacuo gave a heavy oil which was dissolved in 500 ml of water. After basification with ammonia the aqueous solution was extracted with 3×300 ml of dichloromethane. The organic phase was dried over magnesium sulphate, and removal of the solvent in vacuo gave crude 77 as a heavy yellow oil. Yield: 63.0 g (0.320 mol, 81%).

Workup

  1. filtrationFiltration and evaporation in vacuo
  2. customgave a heavy oil which
  3. extractionAfter basification with ammonia the aqueous solution was extracted with 3×300 ml of dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulphate, and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-894423f8d80e4f5894134bad569f8a14
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

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