Nicotinic Acid → HCID 67325240, compound

HRID 82497Notes

Reaction equation

HRID 82497 reaction equation
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.CN1CCOCC1.[CH3:17][CH:18]([CH2:20][C@H:21]([NH2:26])[C:22]([O:24][CH3:25])=[O:23])[CH3:19].Cl>C(Cl)Cl>[CH3:25][O:24][C:22](=[O:23])[C:21]([NH2:26])([C:7]([C:3]1[CH:4]=[N:5][CH:6]=[CH:1][CH:2]=1)=[O:9])[CH2:20][CH:18]([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 79724-MethylmorpholineHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 67325240HCID 67325240, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of niacin (1.35 g, 11.0 mmol) in DCM (20 mL) were added N-methyl morpholine (3.34 g, 33.00 mmol) EDCI.HCl (4.2 g, 22.02 mmol), and L-leucinemethyl ester hydrochloride (2.0 g, 11.0 mmol). The mixture was allowed to stir at room temperature (25° C.) over 2.5 h under nitrogen atmosphere. The resulting mixture was diluted with DCM (200 mL), washed with water (3×100 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 white solid (2.0 g, 72%).

Workup

  1. washwashed with water (3×100 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-fc896c23da2242d7900eafd518759ae6
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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