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Hydrochloric Acid → (13E)-(9alpha,11alpha,15S)-6-Oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

HRID 1277697
ノート
印刷プレビュー

反応式

HRID 1277697 の反応式
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7](Br)[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.C1CCN2C(=NCCC2)CC1.Cl.[OH2:52]>>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:52])[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C@@H:11]1[OH: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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737122(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

生成物 1

HCID 70575053(13E)-(9alpha,11alpha,15S)-6-Oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

反応条件

温度
0 °C

実験手順

Under an atmosphere of nitrogen, a solution of 970 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester (prepared as described in Reference Example 1) and 2 ml of DBU was stirred at room temperature overnight, and then cooled to 0° C. 6 ml of water was added to the reaction mixture, which was then acidified to pH 1 with 1 N hydrochloric acid at 0° C., and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure to give the crude title compound having the following physical characteristic:

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium bicarbonate
  3. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c228b43b2e3b4ba7831de743a7f3172e
出典データセット
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04278688

反応ノート

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