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

HRID 932031
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HRID 932031 반응식
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
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-add401b3dca344a2b608a1275b6fdfbe
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296736B2

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