Oxalic Acid → (4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid

HRID 434738노트

반응식

HRID 434738 반응식
C[O:2][C:3](=[O:38])[CH2:4][CH2:5]/[CH:6]=[CH:7]/[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.[OH-].[K+].C(O)(=O)C(O)=O>CO>[O:37]1[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][CH:8]1/[CH:7]=[CH:6]/[CH2:5][CH2:4][C:3]([OH:38])=[O:2]

참가 물질

5

반응물 3

HCID 971Oxalic AcidHCID 14797Potassium HydroxideHCID 86738984(4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid methyl ester

생성물 1

HCID 86738985(4E,13E)-(6RS,9alpha,11alpha,15S)-6,9-Epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid수율 98.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 480 mg of (4E,13E)-(6RS,9α,11α,15S)-6,9-epoxy-11,15-bis(tetrahydropyran-2-yloxy)prosta-4,13-dienoic acid methyl ester (prepared as described in Example 7) in 3 ml of methanol was added 5 ml of a 5% aqueous solution of potassium hydroxide at 45° to 50° C., and the mixture was stirred for one hour at the same temperature. The reaction mixture was then acidified to pH 5 to 6 with an aqueous solution of oxalic acid and 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 ethanol (20:1) as eluent to give 460 mg of the title compound having the following physical characteristics:

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of cyclohexane and ethanol (20:1) as eluent

출처 및 근거

ORD 기록
ord-10319c8747864fb4b46b71159abf1edb
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04399147

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