Water → 2-Methyl-2-(methylsulfonyl)butanamide

HRID 533545노트

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HRID 533545 반응식
[CH3:1][C:2]([S:30]([CH3:33])(=[O:32])=[O:31])([CH2:13][CH2:14]C1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1)[C:3]([NH:5]OC1CCCCO1)=[O:4].BrC1C=CC(C2ON=C(CO)C=2)=CC=1.[F-].[Cs+].O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:1][C:2]([S:30]([CH3:33])(=[O:31])=[O:32])([CH2:13][CH3:14])[C:3]([NH2:5])=[O:4]

참가 물질

8

반응물 4

HCID 962WaterHCID 25953Cesium fluorideHCID 16641471(5-(4-Bromophenyl)-3-isoxazolyl)methanolHCID 764453942-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-butyramide

생성물 1

HCID 866687702-Methyl-2-(methylsulfonyl)butanamide

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
115 °C

실험 절차

To flask containing 2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanamide, which may be prepared as in Preparation 3, (100 mg, 0.208 mmol) was added [5-(4-Bromo-phenyl)-isoxazol-3-yl]-methanol (58.2 mg, 0.229 mmol), cesium fluoride (126 mg, 0.832 mmol), water (200 uL) and 1,4-dioxane (2 mL). To this mixture was added Palladium tetrakis (35.8 mg, 0.031 mmol) and the mixture was heated to 115° C. with stirring for 3 hours. The mixture was diluted with ethyl acetate and washed with aqueous HCl (0.1 N). The phases were separated and the crude organic extract was concentrated to dryness. The crude material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford N-hydroxy-4-{4′-[3-hhydroxymethyl)isoxazol-5-yl]biphenyl-4-yl}-2-methyl-2-(methylsulfonyl)butanamide as a solid 21 mg.

후처리

  1. custommay be prepared as in Preparation 3, (100 mg, 0.208 mmol)
  2. washwashed with aqueous HCl (0.1 N)
  3. customThe phases were separated
  4. extractionthe crude organic extract
  5. concentrationwas concentrated to dryness
  6. customThe crude material was purified via silica gel chromatography
  7. washeluting with ethyl acetate/heptanes

출처 및 근거

ORD 기록
ord-69c2eab377e44ec1a247a2b89246fcb7
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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