Ammonium Acetate → tert-Butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 417382

反応式

HRID 417382 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=O)[NH:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:30]>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[NH:30][C:16]([C:18]3[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=3)=[CH:15][N:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 517165Ammonium AcetateHCID 596115123-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 59611262tert-Butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate収率 56.3%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.5 g, 3.6 mmol) and ammonium acetate (1.4 g, 18.2 mmol) in xylene (15 mL) was heated in a sealed tube at 140° C. for 2 hours. The volatile component was removed in vacuo, and the residue was dissolved in ethyl acetate (150 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a white solid (795 mg, 56%). m/z 391.8, 393.8 (M+H)+.

後処理

  1. customThe volatile component was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-aa14c2ce82814ce2a24e8f5213c3074e
出典データセット
uspto-grants-2012_01
特許番号
US08088368B2

関連ノート

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