Tetrahydrofuran → 2-(4-tert-Butylphenoxy)-N-((1R)-1-{3-methyl-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide

HRID 1350859Notes

Reaction equation

HRID 1350859 reaction equation
O1CCCC1.[C:6]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([OH:18])=O)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].Cl.[NH2:22][C@@H:23]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=1)[CH3:24]>C(N(CC)CC)C>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]([NH:22][C@@H:23]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=2)[CH3:24])=[O:18])=[CH:19][CH:20]=1)([CH3:7])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 21097519N-{4-[(1R)-1-aminoethyl]-2-methylphenyl)methanesulfonamide hydrochloride

Product 1

HCID 115969052-(4-tert-Butylphenoxy)-N-((1R)-1-{3-methyl-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamideYield 31%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a tetrahydrofuran (THF) (2.0 ml) solution of (4-tert-butylphenoxy)acetic acid (140 mg, 0.7 mmol) 1,1′-dicarbonyldiimidazole (110 mg, 0.7 mmol) was added and the mixture was stirred for 1 hour at ambient temperature. N-{4-[(1R)-1-aminoethyl]-2-methylphenyl}methanesulfonamide hydrochloride (180 mg, 0.7 mmol) and triethylamine (0.5 ml) were added to the mixture. After being stirred for 1 hour at ambient temperature, white precipitate appeared. It was filtered and the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with methylene dichloride/ethyl acetate=1/1 to furnish 90 mg (31% yield) of the title compound as a white solid.

Workup

  1. stirringAfter being stirred for 1 hour at ambient temperature
  2. filtrationIt was filtered
  3. customthe solvent was removed under reduced pressure
  4. customto give a residue, which
  5. washeluted with methylene dichloride/ethyl acetate=1/1

Sources & evidence

ORD record
ord-0f581c58105e4d6ebf701a619dc5ca96
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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