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

HRID 533545ノート

反応式

HRID 533545 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 866687702-Methyl-2-(methylsulfonyl)butanamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
115 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-69c2eab377e44ec1a247a2b89246fcb7
出典データセット
uspto-grants-2014_10
特許番号
US08853258B2

反応ノート

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