Tetrahydrofuran → (13E)-(6RS,9alpha,11alpha,15S)-6,9-Epithio-11,15-dihydroxyprost-13-enoic acid 2-hydroxyethyl ester
반응식
[S:1]1[C@H:12]2[CH2:13][C@@H:14]([OH:25])[C@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]2[CH2:10][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[O:26]1CC[CH2:28][CH2:27]1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>OCCO>[OH:26][CH2:27][CH2:28][O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[S:1][C@H:12]2[CH2:13][C@@H:14]([OH:25])[C@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]2[CH2:10]1참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
실험 절차
A mixture of 70 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid (prepared as described in Example 2), 3 ml of tetrahydrofuran and 34.5 μl of triethylamine was stirred at room temperature for 5 minutes, and then stirred with 27.7 μl of pivaloyl chloride. To the mixture were added 70 μl of triethylamine and 0.5 ml of 2-hydroxyethanol, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, washed with water, and a saturated 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 ethyl acetate and cyclohexane (2:1) as eluent to give 92 mg of the title compound having the following physical characteristics:
후처리
- stirringthe mixture was stirred at room temperature for 18 hours
- washwashed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using
- additiona mixture of ethyl acetate and cyclohexane (2:1) as eluent
출처 및 근거
- ORD 기록
- ord-02fb4dce440447cdb28ca55566923f8c
- 출처 데이터셋
- uspto-grants-1983_01
- 특허 번호
- US04367237
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