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Hydrochloric Acid → (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627265
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HRID 627265 반응식
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([CH2:31][O:32][CH3:33])[CH:20]=[C:19]1[C:34](=[O:37])[NH:35][CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].Cl>O1CCOCC1>[CH2:1]([O:4][N:5]([C@@H:18]1[C:19]([C:34]([NH:35][CH3:36])=[O:37])=[CH:20][C@@H:21]([CH2:31][O:32][CH3:33])[NH:22][CH2:23]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]
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HCID 313Hydrochloric AcidHCID 89852105(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(methoxymethyl)-4-(methylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89852470(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide수율 69%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(methoxymethyl)-4-(methylcarbamoyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 256, 1 g, 1.85 mmol) in dioxane (10 ml) at room temperature was added 4M HCl in Dioxane (2 ml, 57.16 mmol). The reaction mixture was stirred at that temperature for 4-5 hours. The reaction mixture was concentrated and the crude was taken up in 2M NaOH and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Silica gel chromatography (increasing percentage of methanol in dichloromethane) afforded the title compound as a thick oil (0.56 g, 69%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureSilica gel chromatography (increasing percentage of methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-1c621a2215d944bb848a267f6a40a771
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309245B2

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