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Triethylamine → (S)-Hexahydro-3-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-2-oxo-1H-azepine-1-acetic acid, ethyl ester

HRID 484760
ノート
印刷プレビュー

反応式

HRID 484760 の反応式
[CH2:1]([O:3][P:4](Cl)([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2].Cl.[NH2:18][CH:19]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:20]1=[O:32].C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:3][P:4]([NH:18][C@H:19]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:20]1=[O:32])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15591238Ethoxy(4-phenylbutyl)phosphinyl chlorideHCID 1317142923-amino-2-oxo-hexahydro-1H-azepine-1-acetic acid, ethyl ester, monohydrochloride

生成物 1

HCID 86740216(S)-Hexahydro-3-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-2-oxo-1H-azepine-1-acetic acid, ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of ethoxy(4-phenylbutyl)phosphinyl chloride [4.4 mmole; prepared as set forth in Example 1(f)], dry tetrahydrofuran (10 ml.), and 3-amino-2-oxo-hexahydro-1H-azepine-1-acetic acid, ethyl ester, monohydrochloride (1.0 g., 4.0 mmole) at 0° (ice bath) in an argon atmosphere is treated dropwise with triethylamine (1.7 ml., 3.0 eq.) in tetrahydrofuran (5 ml.) over 2 minutes. After 20 minutes, the ice bath is removed and the reaction mixture is stirred for an additional 1.5 hours. The reaction mixture is diluted with ethyl acetate and washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and brine, dried (MgSO4) and evaporated. The residue (2.1 g.) is chromatographed on silica (65 g.) eluting with ethyl acetate then acetone to give 1.0 g. of (S)-hexahydro-3-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-2-oxo-1H-azepine-1-acetic acid, ethyl ester as an oil after evaporation. TLC (ethyl acetate) single spot at Rf =0.1.

後処理

  1. customprepared
  2. customat 0°
  3. customthe ice bath is removed
  4. additionThe reaction mixture is diluted with ethyl acetate
  5. washwashed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue (2.1 g.) is chromatographed on silica (65 g.)
  9. washeluting with ethyl acetate
  10. customacetone to give 1.0 g
  11. customof (S)-hexahydro-3-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-2-oxo-1H-azepine-1-acetic acid, ethyl ester as an oil after evaporation

出典と根拠

ORDレコード
ord-14580fba7e4d474ba4b918e496e78478
出典データセット
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04533661

反応ノート

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