(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester → (13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl ester

HRID 434732노트

반응식

HRID 434732 반응식
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7]([Br:38])[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30]C3CCCCO3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23]C3CCCCO3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH:7]([Br:38])[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([OH:30])[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1

참가 물질

5

반응물 1

HCID 86737122(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

생성물 1

HCID 86738979(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Bromo-6,9-epoxy-11,15-dihydroxyprost-13-enoic acid methyl ester수율 80.3%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

360 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 Example 1) were dissolved in a mixture of 0.7 ml of tetrahydrofuran and 7 ml of 65% aqueous acetic acid and the mixture was stirred at 40° to 45° C. for one hour. The reaction mixture was then diluted with ethyl acetate, washed with water 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 cyclohexane and ethyl acetate (1:3) as eluent to give 210 mg of the title compound having the following physical characteristics:

후처리

  1. washwashed with water
  2. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (1:3) as eluent

출처 및 근거

ORD 기록
ord-b612d572530f4d3496c0f589856f9868
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04399147

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