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

HRID 220104노트

반응식

HRID 220104 반응식
[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

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 86601280(+/-)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5153cb05e6d4949a8bee8cbb4a849e2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202880B2

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