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

HRID 1395855
Notes
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Reaction equation

HRID 1395855 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-cac4422a47934e218893df834988383c
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE045275E1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes