Nicotinic Acid → N-Nicotinoyltyrosine ethyl ester

HRID 2051298Notes

Reaction equation

HRID 2051298 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:26]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH2:31])[CH3:27]>N1C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=1)[NH:31][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)[CH3:27]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 2724939Tyrosine ethyl ester hydrochloride

Product 1

HCID 53849020N-Nicotinoyltyrosine ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Nicotinic acid (12.3 g, 0.1 mol) was dissolved in dry pyridine (300 mL). The solution was cooled and dicyclohexylcarbodiimide (20.6 g, 0.1 mol) was added. After dissolution, tyrosine ethyl ester hydrochloride (24.6 g, 0.1 mol) was added and the solution was stirred overnight. The precipitated dicyclohexylurea (OCU) was removed by filtration. Additional OCU was removed by triturating the oil with hot water. The product was purified with acetone. Calculated for C17H18N2O4 ·1/2H2O: C, 63.16; H, 5.88; N, 8.66. Found: C, 63.10; H, 5.96; N, 8.59. The product can also be named N-[1-ethoxycarbonyl-2-(4'-hydroxyphenyl)ethyl]nicotinamide.

Workup

  1. temperatureThe solution was cooled
  2. additionwas added
  3. customThe precipitated dicyclohexylurea (OCU) was removed by filtration
  4. customAdditional OCU was removed
  5. customby triturating the oil with hot water
  6. customThe product was purified with acetone

Sources & evidence

ORD record
ord-886d1a81cae24738affb946831802cf2
Source dataset
uspto-grants-1991_05
Patent number
US05017566

Reaction notes

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