2-Benzoyl-4-bromobenzoic acid → HCID 23060894, compound

HRID 750365Notes

Reaction equation

HRID 750365 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:40]=[CH:39][C:26]([CH2:27][NH:28][CH2:29][CH:30]([OH:38])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[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)C.C(N(CC)CC)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:38])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:27][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:40][CH:39]=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 23060817HCID 23060817, compound

Product 1

HCID 23060894HCID 23060894, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

[Step 1] 2-Benzoyl-4-bromobenzoic acid (1.0 g) and 1-(4-methanesulfonylbenzylamino)-3-phenylpropan-2-ol (1.1 g) were dissolved in a mixture of THF (10 ml) and acetonitrile (10 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.0 g), 1-hydroxy-1H-benzotriazole monohydrate (0.5 g) and triethylamine (3 ml) were added at room temperature. The reaction 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, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-hexane:ethyl acetate=1:2) to give 2-benzoyl-4-bromo-N-(2-hydroxy-3-phenylpropyl)-N-(4-methanesulfonylbenzyl)benzamide (1.25 g).

Workup

  1. additionwere added at room temperature
  2. concentrationand concentrated under reduced pressure
  3. additionSaturated aqueous sodium hydrogen carbonate was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water, 1N-hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-ad34d45662f04a39acdb49659cbfca64
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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