反应 #1483037

ord-cac4422a47934e218893df834988383c

反应方程式

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
收率 56.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The resulting reaction mixture
  2. 2
    洗涤The organic layer was washed with dilute aqueous NaHCO3, brine
  3. 3
    干燥dried over Na2SO4
  4. 4
    过滤filtered
  5. 5
    浓缩concentrated under reduced pressure
  6. 6
    其他Purification by silica gel chromatography (CH2Cl2)

实验过程

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%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: USRE045275E1uspto-grants-2014_12