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

HRID 484765ノート

反応式

HRID 484765 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0035dbb0b4f4490b838651e9b1dbf5a
出典データセット
uspto-grants-1985_08
特許番号
US04533661

反応ノート

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