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

HRID 421983ノート

反応式

HRID 421983 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:5]=[C:4](C(O)=O)[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:3]=[C:4]([NH:17][C:20]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:34])[N:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 4.62 g of 4-bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid, 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.

後処理

  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

出典と根拠

ORDレコード
ord-a77b296fca1b466899ea0c108700edb7
出典データセット
uspto-grants-2012_01
特許番号
US08101621B2

反応ノート

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