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Hydrogen Peroxide → (4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid methyl ester

HRID 434737
ノート
印刷プレビュー

反応式

HRID 434737 の反応式
[CH3:1][O:2][C:3](=[O:45])[CH2:4][CH2:5][CH2:6][CH:7]([Se]C1C=CC=CC=1)[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1.OO.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3](=[O:45])[CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 86738983(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Phenylseleno-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

生成物 1

HCID 86738984(4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid methyl ester収率 87.8%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 560 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-phenylseleno-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 6) in a mixture of 6 ml of ethyl acetate and 3 ml of tetrahydrofuran was added 0.5 ml of 30% hydrogen peroxide and 100 mg of sodium bicarbonate, and the reaction mixture was then stirred for one hour. Afterwards it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium carbonate, water and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of benzene and ethyl acetate (6:1) as eluent to give 380 mg of the title compound having the following physical characteristics:

後処理

  1. extractionAfterwards it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium carbonate, water
  3. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of benzene and ethyl acetate (6:1) as eluent

出典と根拠

ORDレコード
ord-0720ed4f739e421883eb9a254718f125
出典データセット
uspto-grants-1983_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04399147

反応ノート

読み込み中…

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