Hydrochloric Acid → HCID 86737310、化合物

HRID 224329ノート

反応式

HRID 224329 の反応式
C1CCN2C(=NCCC2)CC1.[CH3:12][O:13][C:14](=[O:39])[CH2:15][CH2:16][CH2:17][CH:18](Br)[CH:19]1[O:37][C@H:22]2[CH2:23][C@@H:24]([OH:36])[C@H:25](/[CH:26]=[CH:27]/[C@@H:28]([OH:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])[C@H:21]2[CH2:20]1.Cl.P([O-])([O-])([O-])=O>C1(C)C=CC=CC=1>[CH3:12][O:13][C:14](=[O:39])[CH2:15][CH2:16][CH2:17]/[CH:18]=[C:19]1/[CH2:20][C@@H:21]2[C@@H:25](/[CH:26]=[CH:27]/[C@@H:28]([OH:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])[C@H:24]([OH:36])[CH2:23][C@@H:22]2[O:37]/1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86737312HCID 86737312、化合物

生成物 1

HCID 86737310HCID 86737310、化合物収率 36.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

Under an atmosphere of nitrogen, 0.1 ml of DBU was added to a solution of 50 mg of (13E)-(5RS,6RS,9α,11α,15S)-5-bromo-6,9-epoxy-11,15-dihydroxy-20-chloroprost-13-enoic acid methyl ester (prepared as described in Example 3) in 0.2 ml of toluene. The mixture was stirred at 50° C. for 1 hour, then at 70° C. for 1.5 hours and then cooled to 0° C. To the reaction mixture were added 0.5 ml of 1 N hydrochloric acid and 0.5 ml of phosphate buffer solution (pH 6.86) with cooling to 0° C. The reaction mixture was extracted quickly with diethyl ether. The extract was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on Florisil using a mixture of ethyl acetate and n-hexane (1:1) containing 0.1% of triethylamine as eluent to give 15 mg of the title compound having the following physical characteristics:

後処理

  1. waitat 70° C. for 1.5 hours
  2. temperaturecooled to 0° C
  3. temperaturewith cooling to 0° C
  4. extractionThe reaction mixture was extracted quickly with diethyl ether
  5. dry with materialThe extract was dried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on Florisil using
  8. additiona mixture of ethyl acetate and n-hexane (1:1)
  9. additioncontaining 0.1% of triethylamine as eluent

出典と根拠

ORDレコード
ord-4f566c6baa204ecf9cdad40262f0723c
出典データセット
uspto-grants-1980_11
特許番号
US04232009

反応ノート

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