تفاعل #1483038

ord-2856cd46971f434281b0e21ca1277ee6

معادلة التفاعل

CC(C)(C)OC(=O)NCCOCCN
tert-Butyl 2-(2-aminoethoxy)ethylcarbamate
O=C(O)c1cccnc1
nicotinic acid
CCN=C=NCCCN(C)C
EDCI
CC(C)(C)OC(=O)NCCOCCNC(=O)c1cccnc1
tert-butyl 2-(2-(nicotinamido)ethoxy)ethylcarbamate
المردود 44.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe resulting reaction mixture
  2. 2
    غسيلwashed with saturated aqueous NaHCO3, brine
  3. 3
    تجفيفdried over Na2SO4
  4. 4
    ترشيحfiltered
  5. 5
    تركيزconcentrated under reduced pressure
  6. 6
    أخرىThe resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH)

الإجراء التجريبي

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.

المصدر

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