Hydrochloric Acid → HCID 86738732, 화합물

HRID 1164156노트

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HRID 1164156 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](O)=[O:8].ClC(OCC(C)C)=O.[CH3:34][S:35]([NH-:38])(=[O:37])=[O:36].[Na+].Cl>CN(C)P(N(C)C)(N(C)C)=O.C(N(CC)CC)C.CN(C)C=O>[CH3:34][S:35]([NH:38][C:7](=[O:8])[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]1)(=[O:37])=[O:36]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 13150714Methanesulfonamide sodium saltHCID 86738733(13E)-(6RS,9alpha,11alpha,15S)-6,9-epithio-11,15-dihydroxyprost-13-enoic acid

생성물 1

HCID 86738732HCID 86738732, 화합물수율 62.1%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 12679Hexamethylphosphoramide용매

실험 절차

To a mixture of 100 mg of (13E)-(6RS,9α,11α,15S)-6,9-epithio-11,15- dihydroxyprost-13-enoic acid (prepared as described in Example 2), 1.5 ml of N,N-dimethylformamide and 37 μl of triethylamine was added 35 μl of isobutyl chloroformate at 0° C., and the mixture was stirred at that temperature for 25 minutes. To it was added a mixture of 128 mg of sodium methanesulphonylamide and 0.233 ml of hexamethylphosphoramide at room temperature, and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was acidified to pH 4-5 with dilute hydrochloric acid, extracted with ethyl acetate, the extract 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 5% v/v solution of methanol in ethyl acetate as eluent to give 75 mg of the title compound having the following physical characteristics.

후처리

  1. additionTo it was added
  2. stirringthe mixture was stirred at ambient temperature for 20 hours
  3. extractionextracted with ethyl acetate
  4. washthe extract washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using a 5% v/v solution of methanol in ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-c9cad2715f8b49e38f86ac0e5d7ae6fe
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04367237

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