Sodium Hydroxide → 5-Methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester

HRID 924601ノート

反応式

HRID 924601 の反応式
[CH2:1]([O:3][C:4]([NH:6][NH:7][C:8](=[O:19])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])=[O:5])[CH3:2].[OH-].[Na+].CS(O[CH2:27][CH2:28][N:29]([O:37][CH3:38])[CH2:30][CH2:31]OS(C)(=O)=O)(=O)=O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4]([N:6]1[CH2:31][CH2:30][N:29]([O:37][CH3:38])[CH2:28][CH2:27][N:7]1[C:8](=[O:19])[CH2:9][C:10]1[C:11]([CH3:18])=[CH:12][C:13]([CH3:17])=[CH:14][C:15]=1[CH3:16])=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 71145194N'-[2-(2,4,6-Trimethyl-phenyl)-acetyl]-hydrazinecarboxylic acid ethyl esterHCID 86719909Methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester

生成物 1

HCID 867199175-Methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

To a vigorously stirred suspension of N′-[2-(2,4,6-trimethyl-phenyl)-acetyl]-hydrazinecarboxylic acid ethyl ester (4.22 g, 15.96 mmol) in toluene (80 ml) was added aqueous sodium hydroxide (12 ml, 30% NaOH w/w in water) and tetra-butyl ammonium bromide (160 mg, 0.48 mmol) at room temperature, followed by methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester (4.66 g, 16.00 mmol) dropwise over 15 minutes at 65° C. The reaction mixture was heated at 65° C. for 6.5 hours. After cooling, the layers were separated, the organic phase evaporated, the residue dissolved in ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate/dichloromethane 5:4:1). Yield: 2.6 g of 5-methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester (compound P3.1) as a colorless oil.

後処理

  1. temperatureAfter cooling
  2. customthe layers were separated
  3. customthe organic phase evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate/dichloromethane 5:4:1)

出典と根拠

ORDレコード
ord-2990e317e520401c94519301f4422b41
出典データセット
uspto-grants-2016_03
特許番号
US09282743B2

反応ノート

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