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

HRID 932031Notes

Reaction equation

HRID 932031 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-add401b3dca344a2b608a1275b6fdfbe
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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