Sodium Hydroxide → HCID 178434012、化合物

HRID 49388ノート

反応式

HRID 49388 の反応式
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](=O)[NH2:19])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].CO[C:24](OC)([N:26](C)C)[CH3:25].O.[NH2:32]N.[OH-].[Na+]>O>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:26][C:24]([CH3:25])=[N:32][N:19]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 5222140tert-butyl N-[2-[4-(2-amino-2-oxoethyl)phenoxy]ethyl]carbamate

生成物 1

HCID 178434012HCID 178434012、化合物収率 59%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

tert-Butyl-[2-(4-carbamoylmethyl-phenoxy)-ethyl]-carbamate (605 mg, 2.05 mmol) and N,N-dimethylacetamide dimethylacetal (5 ml) were combined and heated to about 120° C. for about ninety minutes. The orange solution was then allowed to cool to room temperature and was concentrated in vacuo. The resulting oil was then dissolved in acetic acid (6 ml), and hydrazine hydrate (0.20 ml, 4.10 mmol) was added to the solution. The mixture was heated to about 90° C. for about ninety minutes and was then poured into water and brought to pH 7 by adding 5M sodium hydroxide. The material was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (silica gel; chloroform to 4% methanol/chloroform) to afford 403 mg (59% yield) of the desired product. LRMS ([M+H]+)=333.2.

後処理

  1. temperatureto cool to room temperature
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe resulting oil was then dissolved in acetic acid (6 ml)
  4. temperatureThe mixture was heated to about 90° C. for about ninety minutes
  5. customThe material was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material was purified by column chromatography (silica gel; chloroform to 4% methanol/chloroform)

出典と根拠

ORDレコード
ord-9d8c8ce6fe534ca78ef11d6266aeae7b
出典データセット
uspto-grants-2004_03
特許番号
US06706743B2

反応ノート

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