Binol → HCID 3013585, compound

HRID 856565Notes

Reaction equation

HRID 856565 reaction equation
C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3[OH:21])C2=CC=1.[CH2:23]([O:27][CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:38]=[CH:39][C:40]3[N:46]([CH2:47][CH2:48][CH3:49])[CH2:45][CH2:44][C:43]([C:50]([NH:52][C:53]4[CH:58]=[CH:57][C:56]([S:59][CH2:60][C:61]5[N:65]([CH2:66][CH2:67][CH3:68])[CH:64]=[N:63][N:62]=5)=[CH:55][CH:54]=4)=[O:51])=[CH:42][C:41]=3[CH:69]=2)=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH3:26].[O-]O.[O-]O.C1(C(C)C)C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH2:23]([O:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]2[CH:38]=[CH:39][C:40]3[N:46]([CH2:47][CH2:48][CH3:49])[CH2:45][CH2:44][C:43]([C:50]([NH:52][C:53]4[CH:54]=[CH:55][C:56]([S:59]([CH2:60][C:61]5[N:65]([CH2:66][CH2:67][CH3:68])[CH:64]=[N:63][N:62]=5)=[O:21])=[CH:57][CH:58]=4)=[O:51])=[CH:42][C:41]=3[CH:69]=2)=[CH:35][CH:36]=1)[CH2:24][CH2:25][CH3:26]

Participants

9

Reactant 5

HCID 11762BinolHCID 18500Perhydroxyl radicalHCID 24477Sodium ThiosulfateHCID 53627471Cumen hydroperoxideHCID 69521425HCID 69521425, compound

Product 1

HCID 3013585HCID 3013585, compoundYield 420.5%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of (S)-(−)-1,1′-bi-2-naphtol (87.5 mg) in toluene (10 ml) were added titanium tetraisopropoxide (45.2 μl) and water (55 μl) at room temperature and the mixture was stirred for 1 hour. To the reaction solution were added 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(4-propyl-4H-1,2,4-triazol-3-ylmethylthio)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (1.0 g) and cummene hydroperoxide (80%, 0.31 ml) and the mixture was stirred for 20 hours at room temperature Cumene hydroperoxide (80%, 0.14 ml) was added to the mixture, and the mixture was further stirred for 10 hours. To the reaction solution was added an aqueous solution of sodium thiosulfate and the mixture was stirred for several minutes and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (basic silica gel, ethyl acetate→ethanol:ethyl acetate 1:19), to give (−)-7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-(4-propyl-4H-1,2,4-triazol-3-ylmethylsulfinyl)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 177) (860.9 mg) as yellow amorphous.

Workup

  1. additionwas added to the mixture
  2. stirringthe mixture was further stirred for 10 hours
  3. stirringthe mixture was stirred for several minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with sodium bicarbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was separated
  9. custompurified by column chromatography (basic silica gel, ethyl acetate→ethanol:ethyl acetate 1:19)

Sources & evidence

ORD record
ord-1468f6003b634a2ba966e82ea619a93a
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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