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Diisopropylethylamine → (E)-N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-2-phenylethenesulfonamide

HRID 932037
Notes
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Reaction equation

HRID 932037 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:18]=[CH2:19])[C@@H:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH2:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH:29](/[S:37](Cl)(=[O:39])=[O:38])=[CH:30]\[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:18]=[CH2:19])[C@H:9]([NH:10][S:37](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:39])=[O:38])[C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5369377(E)-2-phenylethene-1-sulfonyl chlorideHCID 58573105(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine

Product 1

HCID 58573743(E)-N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-2-phenylethenesulfonamide

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.33 g (18.24 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine (Example 115, Step E) in DCM (45.0 mL) was added N,N-diisopropylethylamine (4.8 mL, 27.5 mmol), followed by trans-beta-styrenesulfonyl chloride (4.17 g, 20.58 mmol). The resulting solution was stirred at ambient temperature under an N2 atmosphere. After being stirred for 3.25 hours, the reaction was diluted with water and extracted with DCM. The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. Purification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes gradient) provided the title compound as a yellow solid.

Workup

  1. stirringAfter being stirred for 3.25 hours
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with sat. aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customPurification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-f586434719f94699ac590bdf1936089b
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296736B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes