Benzyloxyamine hydrochloride → 1-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid

HRID 730479ノート

反応式

HRID 730479 の反応式
C([O:4][C:5]([C:7]1[N:8]([NH:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1)=[O:6])C=C.Cl.C(ON)C1C=CC=CC=1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:13][NH:12][N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]([OH:6])=[O:4]

参加物

5

反応物 2

HCID 102312Benzyloxyamine hydrochlorideHCID 598535701-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid allyl ester

生成物 1

HCID 598535861-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid収率 82%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 1-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid allyl ester (Example 1c, 2.8 g, 16 mmol) in dichloromethane (70 mL) was added O-benzylhydroxylamine hydrochloride (2.56 g, 16 mmol). Tetrakis(triphenylphosphine)palladium(0) (3.6 g, 3.2 mmol) was added and the reaction mixture was heated at reflux for 16 h. The crude mixture was allowed to cool to 25° C. The solvent was removed in vacuo and redissolved in ethyl acetate (150 mL) and then washed with 10% aqueous hydrochloric acid solution (3×50 mL) and water (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (Merck silica gel 60, 40-63 μm, ethyl acetate/hexane, 20-60%) to afford the desired product, 1-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid (2.5 g, 13 mmol, 82% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 0.94 (6H, d, J=6.4 Hz), 1.41-1.47 (2H, q, J=15.2 Hz, J2=6.8 Hz), 1.68 (1H, m), 6.18 (1H, dd, J1=4.0 Hz, J2=2.8 Hz), 6.98-7.02 (2H, m).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. customThe solvent was removed in vacuo
  4. dissolutionredissolved in ethyl acetate (150 mL)
  5. washwashed with 10% aqueous hydrochloric acid solution (3×50 mL) and water (50 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (Merck silica gel 60, 40-63 μm, ethyl acetate/hexane, 20-60%)

出典と根拠

ORDレコード
ord-270136a2add04419a88373909b1afb62
出典データセット
uspto-grants-2009_09
特許番号
US07582754B2

反応ノート

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