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Hydrochloric Acid → (2r)-N-Hydroxy-2-Methyl-2-(Methylsulfonyl)-4-(2-Oxo-4-Phenylpyridin-1(2h)-Yl)butanamide

HRID 1475830
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HRID 1475830 반응식
Cl.[CH3:2][C@@:3]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][C:17]1=[O:28])[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>O1CCOCC1.O>[OH:7][NH:6][C:4](=[O:5])[C@:3]([CH3:2])([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][C:17]1=[O:28]
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참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 57326796(2R)-2-Methyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

생성물 1

HCID 56593152(2r)-N-Hydroxy-2-Methyl-2-(Methylsulfonyl)-4-(2-Oxo-4-Phenylpyridin-1(2h)-Yl)butanamide

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

HCl (4.0 N in 1,4-dioxane, 20 mL) was added to a solution of (2R)-2-Methyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (5.15 g, 11.5 mmol) in 1,4-dioxane (100 mL) and water (20 mL). The reaction was continued for 2 hours. The reaction was concentrated in vacuo, upon concentration a white solid precipitated. The solid was triturated with 2-propanol (150 mL) at 50° C. for 30 minutes then collected by filtration. The title compound was obtained as a white solid (3.85 g, 92%) LC-MS m/z 365.5 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3H) 2.10-2.23 (m, 1H) 2.37-2.48 (m, 1H) 3.11 (s, 3H) 3.69-3.82 (m, 1H) 4.04-4.19 (m, 1H) 6.63-6.68 (m, 1H) 6.70 (d, J=1.76 Hz, 1H) 7.41-7.55 (m, 3H) 7.68-7.75 (m, 2H) 7.77 (d, J=6.83 Hz, 1H) 11.17 (br. s., 1H). [α]58920=+33.21°.

후처리

  1. concentrationThe reaction was concentrated in vacuo, upon concentration a white solid
  2. customprecipitated
  3. customThe solid was triturated with 2-propanol (150 mL) at 50° C. for 30 minutes
  4. filtrationthen collected by filtration

출처 및 근거

ORD 기록
ord-4454d76e42e64d6d84ba9ec0e2916282
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018384B2

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