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

HRID 434736

反応式

HRID 434736 の反応式
[CH3:1][O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:12][C@@H:11]1[OH:37].C(=O)([O-])[O-].[Ca+2].[C:44]1([Se:50]Br)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.BrBr.C1([SeH-](C2C=CC=CC=2)=[Se])C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6][CH:7]([Se:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:8]1[O:37][C@H:11]2[CH2:12][C@@H:13]([O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:10]2[CH2:9]1

参加物

8

反応物 6

HCID 10112Calcium CarbonateHCID 24408BromineHCID 25517Ammonium ChlorideHCID 123446BromoselenobenzeneHCID 70531213(5Z,13E)-(9alpha,11alpha,15S)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-5,13-dienoic acid methyl esterHCID 178528034HCID 178528034、化合物

生成物 1

HCID 86738983(13E)-(5RS,6RS,9alpha,11alpha,15S)-5-Phenylseleno-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prost-13-enoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of 3.3 g of (5Z,13E)-(9α,11α,15S)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-5,13-dienoic acid methyl ester in 60 ml of tetrahydrofuran was added 610 mg of calcium carbonate at -20° C., and then 6 ml of a solution of benzeneselenenyl bromide in tetrahydrofuran (prepared by adding 0.19 ml of bromine to a solution of 1.25 g of diphenyldiselenide in 6 ml of tetrahydrofuran and stirring the mixture at room temperature for one hour) was added and the reaction mixture was stirred at the same temperature for 10 minutes and further stirred for one hour at 0° C., and then an aqueous solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate. The extract was 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 (7:1) as eluent to give 1.62 g of the title compound having the same physical characteristics as hereinbefore described.

後処理

  1. additionwas added
  2. stirringthe reaction mixture was stirred at the same temperature for 10 minutes
  3. stirringfurther stirred for one hour at 0° C.
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (7:1) as eluent

出典と根拠

ORDレコード
ord-b87e2991a42b4966adc5384fa702d8e5
出典データセット
uspto-grants-1983_08
特許番号
US04399147

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