Hydrazine hydrate (1:1) → (S)-3-[[[2-(benzoylamino)-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

HRID 1285475노트

반응식

HRID 1285475 반응식
C1(=O)[N:5]([CH:6]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:7][P:8]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15]2=[O:26])([O:10][CH2:11][CH3:12])=[O:9])[C:4](=[O:34])[C:3]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:2]12.O.NN>O1CCOCC1>[C:4]([NH:5][CH:6]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:7][P:8]([NH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15]1=[O:26])([O:10][CH2:11][CH3:12])=[O:9])(=[O:34])[C:3]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:2]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 86740219(S)-3-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

생성물 1

HCID 86740220(S)-3-[[[2-(benzoylamino)-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of (S)-3-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester in dioxane is treated with hydrazine hydrate and stirred for 24 hours at room temperature. The mixture is then partitioned between ethyl acetate-water and the ethyl acetate phase is washed with water and saturated sodium chloride, dried (Na2SO4), and evaporated. The residue is taken up in dry toluene and refluxed for one hour. The mixture is filtered, treated with triethylamine and benzoyl chloride and stirred at room temperature for 30 minutes. The mixture is diluted with ethyl acetate, washed successively with 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride, dried (Na2SO4), and evaporated. The residue is chromatographed on silica gel to give (S)-3-[[[2-(benzoylamino)-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester.

후처리

  1. customThe mixture is then partitioned between ethyl acetate-water
  2. washthe ethyl acetate phase is washed with water and saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. temperaturerefluxed for one hour
  6. filtrationThe mixture is filtered
  7. additiontreated with triethylamine and benzoyl chloride
  8. stirringstirred at room temperature for 30 minutes
  9. additionThe mixture is diluted with ethyl acetate
  10. washwashed successively with 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride
  11. dry with materialdried (Na2SO4)
  12. customevaporated
  13. customThe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-1abf055fca684c909ebd36708a780c07
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04567167

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