Hydrochloric Acid → 5-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester

HRID 337228노트

반응식

HRID 337228 반응식
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[O:18]C(C(=O)NCCC3C=CC=CC=3)=C[CH:21]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N(C(C)C)CC)(C)C.[C:44](Cl)(=[O:47])[CH:45]=[CH2:46].[O:49]1CCOC[CH2:50]1>C(Cl)Cl>[CH3:50][O:49][C:44]([C:45]1[O:18][C:17]([S:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:33])[CH2:13][CH2:12]2)(=[O:16])=[O:15])=[CH:21][CH:46]=1)=[O:47]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 71060234[1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 710601525-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester수율 2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.15 g, 0.3 mmol) was suspended in a 4M solution of HCl in Dioxane (5 ml). The resulting suspension was stirred at room temperature for 3 hours. After this time the solution was concentrated under vacuum and the resulting residue dissolved in THF (10 ml). To this solution was added diisopropylethylamine (0.3 ml, 1.6 mmol) was added in one portion, followed by the drop wise addition of acryloyl chloride (0.03 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane) to give the title compound (0.01 g, 2% yield) as a white solid.

후처리

  1. concentrationAfter this time the solution was concentrated under vacuum
  2. dissolutionthe resulting residue dissolved in THF (10 ml)
  3. additionwas added in one portion
  4. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours
  5. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe resulting residue was purified by flash column chromatography (elution: 50% EtOAc, 50% heptane)

출처 및 근거

ORD 기록
ord-3b5bcde2965448b894413c218b38dd4e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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