Sodium Hydroxide → 2-(3,4-dichlorophenyl)-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-2-prop-2-ynyloxy-acetamide

HRID 1375228Notes

Reaction equation

HRID 1375228 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:31])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].S(C1C=CC(C)=CC=1)(O[C:38]#[C:39][CH3:40])(=O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([O:31][CH2:40][C:39]#[CH:38])[C:10]([NH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 3715371-Propynyl 4-methylbenzenesulfonateHCID 116698222-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide

Product 1

HCID 116989762-(3,4-dichlorophenyl)-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-2-prop-2-ynyloxy-acetamide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.4 g (0.85 mmol) of 2-(3,4-dichlorophenyl)-2-hydroxy-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-acetamide, 0.5 ml of 30% aqueous sodium hydroxide solution and 5 mg of tetrabutylammonium bromide in 3 ml dichloromethane is added 0.18 g (0.85 mmol) of propynyl tosylate during 1 hour. Upon completion of the addition the reaction mixture is stirred for additional 16 hours at room temperature. The mixture is then extracted with dichloromethane. The organic extract is concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with 1 :2 ethyl acetate/isohexane as the eluant to obtain 2-(3,4-dichlorophenyl)-N-[trans-2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-cyclohexyl]-2-prop-2-ynyloxy-acetamide.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. extractionThe mixture is then extracted with dichloromethane
  3. extractionThe organic extract
  4. concentrationis concentrated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-d3a78ac70cfb4bf48b4c544ee8cba444
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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