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

HRID 1618369

반응식

HRID 1618369 반응식
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[C:1]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

참가 물질

7

반응물 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 187201N-BOC-ethylenediamine

생성물 1

HCID 47453328Tert-butyl 2-(nicotinamido)ethylcarbamate수율 74%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

In a typical run, nicotinic acid (2.0 g, 16.2 mmol) was taken up in CH2Cl2 (20 mL) along with oxalyl chloride (1.4 mL, 16.2 mmol). After a few drops of DMF were added, the reaction mixture was stirred at room temperature until all the solids had dissolved and all gas evolution had ceased (1 h). This freshly prepared solution of the acid chloride was added dropwise at 0° C. to a solution containing tert-butyl 2-aminoethylcarbamate (2.6 g, 16.2 mmol) and Et3N (3.4 mL, 24.2 mmol) in CH2Cl2 (200 mL). The resulting reaction mixture was warmed to room temperature and stirred for 2 h. It was then washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded tert-butyl 2-(nicotinamido)ethylcarbamate (3.1 g, 74%).

후처리

  1. dissolutionhad dissolved
  2. custom(1 h)
  3. customThe resulting reaction mixture
  4. temperaturewas warmed to room temperature
  5. stirringstirred for 2 h
  6. washIt was then washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by silica gel chromatography (CH2Cl2)

출처 및 근거

ORD 기록
ord-6b7c558b25034676a5912c9421ee68a1
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765964B2

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