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Acetic Acid → (13E)-(11alpha,15S)-6,9-Dioxo-11,15-dihydroxyprost-13-enoic acid methyl ester

HRID 2058304
ノート
印刷プレビュー

反応式

HRID 2058304 の反応式
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23]C2CCCCO2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30]C2CCCCO2)[CH2:12][C:11]1=[O:37].C(O)(=O)C>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:38])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([OH:30])[CH2:12][C:11]1=[O:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 176Acetic AcidHCID 70575454(13E)-(11alpha,15S)-6,9-Dioxo-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

生成物 1

HCID 12899027(13E)-(11alpha,15S)-6,9-Dioxo-11,15-dihydroxyprost-13-enoic acid methyl ester収率 53.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of 480 mg of (13E)-(11α,15S)-6,9-dioxo-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Example 1) in 1 ml of tetrahydrofuran was added 3 ml of 65% (v/v) aqueous acetic acid and the mixture was stirred at 45° C. for 3 hours. The reaction mixture was diluted with 16 ml of water and extracted with a mixture of ethyl acetate and n-hexane (1:1). The extract was washed with water, an aqueous solution of sodium bicarbonate 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 ethyl acetate and n-hexane (1:1) as eluent to give 177 mg of the title compound having the following physical characteristics:

後処理

  1. extractionextracted with a mixture of ethyl acetate and n-hexane (1:1)
  2. washThe extract was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate and an 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 ethyl acetate and n-hexane (1:1) as eluent

出典と根拠

ORDレコード
ord-db1754b64c774c43b8aeb679e4c57478
出典データセット
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04215142

反応ノート

読み込み中…

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