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Nicotinic Acid → Tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamate

HRID 1618348
Notes
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Reaction equation

HRID 1618348 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][S:13][S:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCN=C=NCCCN(C)C>CC#N.CCOC(C)=O>[C:1]([NH:10][CH2:11][CH2:12][S:13][S:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 938Nicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22245556tert-butyl N-(2-((2-aminoethyl)disulfanyl)ethyl)carbamate

Product 1

HCID 86651799Tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamateYield 56%

Reagents, catalysts & solvents 2

HCID 6342Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

Separately, nicotinic acid (246 mg, 2.0 mmol) was taken up in CH3CN (10 mL) along with tert-butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate (503 mg, 2.0 mmol), EDCI (422 mg, 2.2 mmol). The resulting reaction mixture was stirred at room temperature for 4 h and then diluted with EtOAc. The organic layer was washed with dilute aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamate (400 mg, 56%).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with dilute aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-d621213099db46ee85bde9470df167b1
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765963B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes