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

HRID 750363Notes

Reaction equation

HRID 750363 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:37]=[CH:36][C:26]([CH2:27][NH:28][CH2:29][CH:30]([OH:35])[CH2:31][CH2:32][CH2:33][CH3:34])=[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:35])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:37][CH:36]=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 230607631-(4-Methanesulfonylbenzylamino)hexan-2-ol

Product 1

HCID 230606192-benzoyl-4-bromo-N-(2-hydroxyhexyl)-N-(4-methanesulfonylbenzyl)benzamideYield 68.5%

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)hexan-2-ol (1.9 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 mixture was stirred at room temperature for 12 hrs. and concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added to the residue 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. The residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=1:1) to give 2-benzoyl-4-bromo-N-(2-hydroxyhexyl)-N-(4-methanesulfonylbenzyl) benzamide (2.57 g).

Workup

  1. concentrationand concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate was added to the residue
  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. customThe residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-da2844bccd734914a6c84b228705cb1c
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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