تفاعل #1483037

ord-cac4422a47934e218893df834988383c

معادلة التفاعل

O=C(O)c1cccnc1
nicotinic acid
CC(C)(C)OC(=O)NCCSSCCN
tert-butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate
CCN=C=NCCCN(C)C
EDCI
CC(C)(C)OC(=O)NCCSSCCNC(=O)c1cccnc1
tert-butyl 2-(2-(2-(nicotinamido)ethyl)disulfanyl)ethylcarbamate
المردود 56.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe resulting reaction mixture
  2. 2
    غسيلThe organic layer was washed with dilute aqueous NaHCO3, brine
  3. 3
    تجفيفdried over Na2SO4
  4. 4
    ترشيحfiltered
  5. 5
    تركيزconcentrated under reduced pressure
  6. 6
    أخرىPurification by silica gel chromatography (CH2Cl2)

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE045275E1uspto-grants-2014_12