tert-Butanol → Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 2244413ノート

反応式

HRID 2244413 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](C(O)=O)[N:7]=1)=[O:5])[CH3:2].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:17][C:20]([O:43][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:29])[N:7]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 35944446-(Ethoxycarbonyl)picolinic acid

生成物 1

HCID 19349079Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate収率 78%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of pyridine-2,6-dicarboxylic acid monoethyl ester (1.00 g, 5.12 mmol), triethylamine (1.04 g, 10.24 mmol), diphenylphosphoryl azide (DPPA) (1.93 g, 7.02 mmol) and tert-butanol (3.00 ml) in toluene (30.00 ml) was warmed at 100° C. for 20 h. The mixture was then cooled at room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was then dried over sodium sulphate and evaporated. The residue was purified by flash chromatography to yield 6-tert-butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester (1.06 g, 78%) as a viscous orange oil, MS (ISP): m/e=267.3 (M+H+).

後処理

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialThe organic layer was then dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-dc32e2909aef4fe6adb1df949762e70f
出典データセット
uspto-grants-2010_03
特許番号
US07678815B2

反応ノート

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