Nicotinic Acid → Tert-butyl 2-(2-(nicotinamido)ethoxy)ethylcarbamate

HRID 591106Notes

Reaction equation

HRID 591106 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[C:15](O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.CCN=C=NCCCN(C)C>CC#N.CCOC(C)=O>[C:15]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 3

HCID 938Nicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

Product 1

HCID 69811586Tert-butyl 2-(2-(nicotinamido)ethoxy)ethylcarbamateYield 44%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (420, 2.06 mmol) was then taken up in CH3CN (20 mL) along with nicotinic acid (253 mg, 2.06 mmol) and EDCI (434 mg, 2.3 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-(nicotinamido)ethoxy)ethylcarbamate (280 mg, 44%). MS calculated for C15H23N3O4: 309.17. found: [M+H]+ 310.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-205f4ac9893e4f42945819e2e25e7a93
Source dataset
uspto-grants-2016_01
Patent number
US09238077B2

Reaction notes

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