Sodium Hydroxide → HCID 178434012, 화합물

HRID 49388노트

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HRID 49388 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 178434012HCID 178434012, 화합물수율 59%

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9d8c8ce6fe534ca78ef11d6266aeae7b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706743B2

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