m-Chloroperbenzoic acid → (+/-)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide

HRID 30072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30072
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:28]=[CH:29][C:30]=2[O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:9]([NH:11][C@H:12]2[C@@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:16][CH:15]=[CH:14][CH2:13]2)=[O:10])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:44])C=1>ClCCl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:28]=[CH:29][C:30]=2[O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:9]([NH:11][CH:12]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:16][CH:15]3[CH:14]([O:44]3)[CH2:13]2)=[O:10])[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 86601280(+/-)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide2×

Produkt 1

HCID 86601279(+/-)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

37.7 g of (±)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide (compound F1) are dissolved in 470 ml of dichloromethane and treated with 27.4 g of m-chloroperbenzoic acid. After stirring over night at room temperature, the reaction mixture is extracted with sodium hydrogencarbonate solution and water, the organic phase is dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel using a a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1. 26.5 g of the title compound are obtained.

Aufarbeitung

  1. extractionthe reaction mixture is extracted with sodium hydrogencarbonate solution and water
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel using a
  5. additiona mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1

Quellen und Nachweise

ORD-Eintrag
ord-8989c23aae324521b4d7c05260914a74
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423046B2

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