2-Benzoyl-4-bromobenzoic acid → 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide

HRID 750360Notes

Reaction equation

HRID 750360 reaction equation
[C:1]([C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20]([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][NH:28][CH2:29][CH:30]([OH:34])[CH2:31][CH2:32][CH3:33])=[CH:25][CH:24]=1)(=[O:22])=[O:21].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C1COCC1.C(N(CC)CC)C.C(#N)C>[C:1]([C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:10]=1[C:11]([N:28]([CH2:29][CH:30]([OH:34])[CH2:31][CH2:32][CH3:33])[CH2:27][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:36][CH:35]=1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 3467342-Benzoyl-4-bromobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 230607521-(4-Methanesulfonylbenzylamino)pentan-2-ol

Product 1

HCID 230607862-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamideYield 82%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

[Step 1] To a solution (20 ml) of 2-benzoyl-4-bromobenzoic acid (2.0 g) in THF were added 1-(4-methanesulfonylbenzylamino)pentan-2-ol (1.8 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.9 g), 1-hydroxy-1H-benzotriazole monohydrate (1.0 g), acetonitrile (20 ml) and triethylamine (5 ml) at room temperature. The reaction mixture was stirred at room temperature for 12 hrs. and concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crystals were washed with diisopropyl ether to give 2-benzoyl-4-bromo-N-(2-hydroxypentyl)-N-(4-methanesulfonylbenzyl)benzamide (3.0 g).

Workup

  1. concentrationand concentrated under reduced pressure
  2. additionTo the residue was added saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe obtained crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-b8baadd3caf146e2b7b6fa3f611b0860
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…