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

HRID 220104ノート

反応式

HRID 220104 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1. 26.5 g of the title compound are obtained.

後処理

  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
  5. additiona mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1

出典と根拠

ORDレコード
ord-e5153cb05e6d4949a8bee8cbb4a849e2
出典データセット
uspto-grants-2012_06
特許番号
US08202880B2

反応ノート

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