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

HRID 50773

反応式

HRID 50773 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b4e7f44004264174a2fd5c2c996aaf75
出典データセット
uspto-grants-2004_03
特許番号
US06713484B2

関連ノート

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