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

HRID 2244413노트

반응식

HRID 2244413 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-dc32e2909aef4fe6adb1df949762e70f
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678815B2

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