Diethyl Ether → HCID 86759211, compound

HRID 987606Notes

Reaction equation

HRID 987606 reaction equation
[C:1]1([C:7]2([CH2:13][NH:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[O:16])[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.CCOCC>C(Cl)Cl>[O:33]1[C@H:9]2[CH2:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([CH2:13][NH:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])=[O:16])[CH2:12][CH2:11][C@H:10]12

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 18009503HCID 18009503, compound

Product 1

HCID 86759211HCID 86759211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)-cyclohex-1-ene (Example 192, 146.3 mg, 0.46 mmol) and mCPBA (156.8 mg, 0.92 mmol) in 8.0 mL of CH2Cl2 was stirred at rt for 18 h. The reaction mixture was poured into ether, washed with NaHCO3 (3×), dried over Na2SO4, filtered through a plug of silica gel and concentrated The residue was purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm) using a mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 1.0/8.0 mL/min) to give the separated cis and trans isomers.

Workup

  1. washwashed with NaHCO3 (3×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered through a plug of silica gel
  4. concentrationconcentrated The residue
  5. customwas purified by HPLC (Waters RCM, μ Porosil, 25 mm×10 cm)
  6. additiona mixture of (5:4:1 hexane-methyl tert-butyl ether-acetonitrile:hexane, 1.0/8.0 mL/min)
  7. customto give the separated cis and trans isomers

Sources & evidence

ORD record
ord-506e31249e884947b5bf195d41e6ccc1
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

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