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Ethyl Acetate → 6-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HRID 1096357
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HRID 1096357 반응식
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([CH:29]([CH3:31])[CH3:30])OC(=O)[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.CC(C)(C[C@@]1(C2C=CC=CC=2)OC(=O)N([C@H](C2C=CC([C:52]3[CH:57]=[CH:56][NH:55][C:54](=[O:58])[CH:53]=3)=CC=2)C)CC1)C#N.[C:66]([O-:69])([O-])=[O:67].[Cs+].[Cs+].[CH3:72]COC(C)=O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1([CH:29]([CH3:30])[CH3:31])[O:69][C:66](=[O:67])[N:8]([C@H:12]([C:14]2[CH:15]=[CH:16][C:17]([C:52]3[CH:57]=[CH:56][N:55]([CH3:72])[C:54](=[O:58])[CH:53]=3)=[CH:18][CH:19]=2)[CH3:13])[CH2:7][CH2:6]1
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참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 596357032,2-dimethyl-3-((R)-2-oxo-3-((S)-1-(4-(2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-6-yl)propanenitrileHCID 596357376-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

생성물 1

HCID 66735728
6-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 6-(3-hydroxypropyl)-6-isopropyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one (40 mg, 0.092 mmol), 4-iodo-1-methylpyridin-2(1′-O-one (20 mg, 0.085 mmol), Pd(PPh3)2Cl2 (6 mg, 0.0085 mmol), and Cs2CO3 (2 N, 0.425 mL, 0.85 mmol) in 1,4-dioxane (2 mL) was refluxed for 3 h under N2. The reaction mixture was treated with EtOAc (20 mL) and water (20 mL), and the organic layer was dried and concentrated in vacuo. The residue was purified by preparative HPLC to give two isomers.

후처리

  1. temperaturewas refluxed for 3 h under N2
  2. customthe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC
  5. customto give two isomers

출처 및 근거

ORD 기록
ord-25938a9c1cf644c08c4ee786abce8219
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138178B2

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