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Thiophenol → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627266
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HRID 627266 반응식
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:28][O:29][CH3:30])[NH:20][CH2:19]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][C@@H:18]1[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:28][O:29][CH3:30])[NH:20][CH2:19]1)[CH:2]=[CH2:3]
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참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852470(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide2회

생성물 1

HCID 89852327(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide수율 81%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

To a mixture of (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N-methyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 257, 561 mg, 1.27 mmol) and potassium carbonate (880 mg, 6.37 mmol) in acetonitrile (15 mL) at room temperature was added benzenethiol (0.654 mL, 6.37 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated onto silica gel. Silica gel chromatography (0%-20% methanol/dichloromethane) afforded the title compound as an off-white solid (0.26 g, 81%).

후처리

  1. concentrationThe reaction mixture was concentrated onto silica gel

출처 및 근거

ORD 기록
ord-20a2503f9daa4bd2944f98409f185734
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309245B2

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