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Sodium hydride → tert-butyl cis-3-fluoro-4-((4-(N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)sulfamoyl)phenoxy)methyl)piperidine-1-carboxylate

HRID 594137
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HRID 594137 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:21])[CH3:20])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[F:28][C@H:29]1[C@@H:34]([CH2:35][OH:36])[CH2:33][CH2:32][N:31]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30]1>CN(C)C=O>[F:28][C@H:29]1[C@@H:34]([CH2:35][O:36][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH:19]([CH3:20])[CH3:21])=[CH:14][N:13]=3)=[CH:4][CH:3]=2)[CH2:33][CH2:32][N:31]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 89875921(3S,4R)-rel-tert-Butyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylateHCID 898761814-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

생성물 1

HCID 117925923tert-butyl cis-3-fluoro-4-((4-(N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)sulfamoyl)phenoxy)methyl)piperidine-1-carboxylate수율 91.7%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

4-fluoro-N-isobutyl-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide (35 mg, 0.10 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil) followed by tert-butyl cis-3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (22 mg, 0.10 mmol). The reaction was stirred overnight at room temperature, under nitrogen, then quenched with water and concentrated in vacuo. The crude product was extracted to the organic phase of an aqueous workup between ethyl acetate and water. The organic phase was then passed through a hydrophobic frit and concentrated in vacuo to give the title compound (53 mg). LCMS (2 min, formic) Rt 1.53 min, m/z (ES+) 578 (M+H).

후처리

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. extractionThe crude product was extracted to the organic phase of an aqueous workup between ethyl acetate and water
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-69a5669a66b64471b3e17ca4845e6759
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242972B2

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