1,2-Dichloroethane → 2-(4-adamantan-1-yl-phenoxy)-N-(3-methanesulfonyl-phenyl)-acetamide

HRID 1945368Notes

Reaction equation

HRID 1945368 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[CH3:23][S:24]([C:27]1[CH:28]=[C:29]([NH2:33])[CH:30]=[CH:31][CH:32]=1)(=[O:26])=[O:25].CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([NH:33][C:29]4[CH:30]=[CH:31][CH:32]=[C:27]([S:24]([CH3:23])(=[O:26])=[O:25])[CH:28]=4)=[O:18])=[CH:20][CH:21]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8HCID 27351793-(Methylsulfonyl)aniline hydrochloride

Product 1

HCID 248108932-(4-adamantan-1-yl-phenoxy)-N-(3-methanesulfonyl-phenyl)-acetamideYield 816.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 3-methanesulfonyl-phenylamine hydrochloride (54.39 mg, 0.26 mmol) and DIPEA (33.85 mg, 0.26 mmol) in DMF (2 mL) was added EDC (50.2 mg, 0.26 mmol) and HOBt (35.39 mg, 0.26 mmol) at room temperature. The reaction mixture was stirred at room temperature until completion and then poured into water (100 mL). The resulting solid was extracted with ethyl acetate, washed with brine, aqueous sodium bicarbonate and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (Ethyl acetate:hexanes=2:8 to 4:6) to afford 2-(4-adamantan-1-yl-phenoxy)-N-(3-methanesulfonyl-phenyl)-acetamide as a colorless solid (0.61 g, 80% yield).

Workup

  1. extractionThe resulting solid was extracted with ethyl acetate
  2. washwashed with brine, aqueous sodium bicarbonate and water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by flash chromatography on silica gel (Ethyl acetate:hexanes=2:8 to 4:6)

Sources & evidence

ORD record
ord-7089e0c6262248018a5293d7f3d384ea
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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