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Pyridine 4-methylbenzene-1-sulfonate → (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid

HRID 326183
ノート
印刷プレビュー

反応式

HRID 326183 の反応式
[Cl:1][C@H:2]1[CH2:15][C@@H:14]([O:16]C2CCCCO2)[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([O:33]C2CCCCO2)[CH:26]([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(O)C.C(Cl)Cl>[Cl:1][C@H:2]1[CH2:15][C@@H:14]([OH:16])[C@H:13](/[CH:23]=[CH:24]/[C@@H:25]([OH:33])[CH:26]([CH3:32])[CH2:27][CH:28]=[C:29]([CH3:30])[CH3:31])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]
参加物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 161440Pyridine 4-methylbenzene-1-sulfonateHCID 67859606(5Z,13E)-(8R,9S,11R,-12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid

生成物 1

HCID 67859588(5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid収率 42%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

A solution of 144 mg of (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid in 2 ml of absolute ethanol was combined with 6.4 mg of pyridine p-toluenesulfonate and agitated for 5 days at room temperature under argon. The reaction mixture was then diluted with 100 ml of methylene chloride, washed twice with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent, thus obtaining 42.5 mg of the desired carboxylic acid as a highly viscous oil.

後処理

  1. washwashed twice with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness under vacuum
  4. customThe residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-c98d9cf42f884f8caf14e63d9f3ac74f
出典データセット
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04444788

反応ノート

読み込み中…

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