Hydrochloric Acid → HCID 86737310, 화합물

HRID 224329노트

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HRID 224329 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 86737310HCID 86737310, 화합물수율 36.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-4f566c6baa204ecf9cdad40262f0723c
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04232009

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