Carbon Dioxide → 4-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

HRID 50773

반응식

HRID 50773 반응식
C([Li])CCC.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].CCOCC.[C:25](=[O:27])=[O:26]>C1COCC1.C(O)(=O)C.O>[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([C:25]([OH:27])=[O:26])=[CH:16][N:17]=[CH:18][CH:19]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 99902104-(Boc-amino)pyridineHCID 178418339Butyllithium

생성물 1

HCID 221726234-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid수율 54%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

n-Butyl lithium (2.18 M, 24 mL, 52.51 mmol) is added slowly to a solution of 4-(N-t-butoxycarbonylamino)-pyridine (4.08 g, 21 mmol) in THF (50 mL, stirred under N2 at −78° C. The solution is allowed to warm to 0° C., stirred for 3 h, then cooled again to −78° C. and poured into ether (100 mL) containing dry ice. The solution is warmed to room temperature with constant stirring. Water is added and the mixture is neutralized with acetic acid. The resulting solid is collected by vacuum filtration and dried in a vacuum oven to give 4-(N-t-butoxycarbonylamino)nicotinic acid (2.72 g, 54%) as a brown solid. 1H NMR (DMSO) δ 11.75 (1H, brs), 8.95 (1H, s), 8.50 (1H, d, J=6.0 Hz) 8.20 (1H, d, J=6.0 Hz), 1.49 (9H, s).

후처리

  1. temperatureto warm to 0° C.
  2. stirringstirred for 3 h
  3. temperaturecooled again to −78° C.
  4. temperatureThe solution is warmed to room temperature with constant stirring
  5. filtrationThe resulting solid is collected by vacuum filtration
  6. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-b4e7f44004264174a2fd5c2c996aaf75
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713484B2

연결된 노트

불러오는 중…