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Ethyl Acetate → N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamide

HRID 932031
ノート
印刷プレビュー

反応式

HRID 932031 の反応式
C(OC1C=CC=CC=1C[N:12]([C@H:16]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C@@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[CH:18]=[CH2:19])[C:13](=[O:15])[CH3:14])(=O)C.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:26][C:22]1[CH:21]=[C:20]([C@@H:17]([CH:18]=[CH2:19])[C@H:16]([NH:12][C:13](=[O:15])[CH3:14])[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=1
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 8857Ethyl AcetateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 585738512-((N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamido)methyl)phenyl acetate

生成物 1

HCID 58573475N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1.05 g (2.18 mmol) of 2-((N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)acetamido)methyl)phenyl acetate (Example 115, Step C) and toluenesulfonic acid monohydrate (1.66 g, 8.71 mmol) in toluene (15.0 mL) was heated to reflux for about 2 h. 120 ml of ethyl acetate was added, and the combined organics were washed consecutively with NaHCO3 solution and sat. NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The crude mixture was purified by preparative HPLC to give the title compound.

後処理

  1. temperatureto reflux for about 2 h
  2. washthe combined organics were washed consecutively with NaHCO3 solution and sat. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe crude mixture was purified by preparative HPLC

出典と根拠

ORDレコード
ord-add401b3dca344a2b608a1275b6fdfbe
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296736B2

反応ノート

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