tert-Butanol → Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 1172425노트

반응식

HRID 1172425 반응식
[Br:1][C:2]1[CH:7]=[C:6](C(O)=O)[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.C([N:17]([CH2:20]C)CC)C.[C:22]([OH:26])([CH3:25])([CH3:24])[CH3:23].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1>O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:17][C:20]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:34])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 469414564-Bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid

생성물 1

HCID 25067269Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of 4.62 g of methyl hydrogen 4-bromopyridine-2,6-dicarboxylate, 2.97 ml of triethylamine, 25 ml of t-butanol and 70 ml of 1,4-dioxane was added 4.59 ml of diphenylphosphoryl azide at room temperature. The reaction mixture was heated under reflux for 3 hours and cooled to room temperature. Water was added thereto and the resulting mixture was extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe obtained ethyl acetate solution was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-7fd21717c6d14f91a36b46b34fec5178
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834018B2

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