HCID 18689654, compound → HCID 54214489, compound

HRID 1872266Notes

Reaction equation

HRID 1872266 reaction equation
[CH:1]([O:14][N:15]1[C:24](=[O:25])[CH:23]2[CH:17]([N:18]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH2:19][CH:20]=[CH:21][CH2:22]2)[C:16]1=[O:37])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]1([Mg]Br)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1.C(OCC)C>[CH:1]([O:14][NH:15][C:16]([CH:17]1[CH:23]([C:24](=[O:25])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:22][CH:21]=[CH:20][CH2:19][N:18]1[S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27])=[O:37])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 18689654HCID 18689654, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 54214489HCID 54214489, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

7-Benzhydryloxy-1-(4-methoxybenzenesulfonyl)-2,5,5a,8a-tetrahydro-1H-pyrrolo[3,4-b]azepine-6,8-dione (100 mg, 0.19 mmol) was dissolved in THF (2 mL) and cooled to -78° C. This solution was treated dropwise with a 3 M solution of phenyl magnesium bromide in diethyl ether and then warmed to ambient temperature. The reaction mixture was stirred another 2.5 hrs at room temperature, cooled to 0° C., and quenched with saturated aqueous NH4Cl (2 mL). This mixture was then diluted with H2O and diethyl ether and the layers were separated. The organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 5 to 10% ethyl acetate in toluene) to give 3-benzoyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid benzhydryloxy-amide; MS: (M+H)+ 596.9, (M+NH4)+ 614.2.

Workup

  1. temperaturewarmed to ambient temperature
  2. temperaturecooled to 0° C.
  3. customquenched with saturated aqueous NH4Cl (2 mL)
  4. additionThis mixture was then diluted with H2O and diethyl ether
  5. customthe layers were separated
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (silica, 5 to 10% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-36fcc89dc4e24e6380b6f32ee71eb2f8
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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