Triethylamine → N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-N-(dicyclopropylmethyl)acrylamide

HRID 932034Notes

Reaction equation

HRID 932034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:25]=[CH2:26])[C@@H:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[NH:10][CH:11]([CH:15]2[CH2:17][CH2:16]2)[CH:12]2[CH2:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36].C(OCC)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:25]=[CH2:26])[C@H:9]([N:10]([CH:11]([CH:12]2[CH2:13][CH2:14]2)[CH:15]2[CH2:16][CH2:17]2)[C:34](=[O:37])[CH:35]=[CH2:36])[C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 13140Acryloyl chlorideHCID 67999637(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine

Product 1

HCID 67999897N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-N-(dicyclopropylmethyl)acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.1 g (5.44 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine (Example 115, Step F) and triethylamine (1.89 mL, 13.59 mmol) in THF (30.0 mL) was added acryloyl chloride (0.66 mL, 8.15 mmol) at 0° C. The resulting reaction mixture was stirred at rt for 2 h. When LCMS indicated completion of the reaction, 100 ml of ethyl acetate was added and the combined organics were washed consecutively with water (10 ml), citric acid (10 ml, 1M), NaHCO3 solution (10 ml) and sat. NaCl solution (30 ml), dried over MgSO4, filtered and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate, 90/10 to 20/80) to give the title compound.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. washthe combined organics were washed consecutively with water (10 ml), citric acid (10 ml, 1M), NaHCO3 solution (10 ml) and sat. NaCl solution (30 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate, 90/10 to 20/80)

Sources & evidence

ORD record
ord-e2f976e4473d4e289d6d4291e92f5cdf
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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