Diisopropylethylamine → 3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide

HRID 1881820ノート

反応式

HRID 1881820 の反応式
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.Cl.[CH:55]([C:58]1[O:62][N:61]=[CH:60][C:59]=1[NH2:63])([CH3:57])[CH3:56]>CN(C)C=O.O>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([NH:63][C:59]2[CH:60]=[N:61][O:62][C:58]=2[CH:55]([CH3:57])[CH3:56])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acidHCID 684313035-(Propan-2-yl)-1,2-oxazol-4-amine hydrochlorideHCID 178484293HCID 178484293、化合物

生成物 1

HCID 593312733-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution (15 ml) of 3-cyclopentyl-2-[4-(methylsulfonyl)phenyl]propanoic acid (2.00 g) in N,N-dimethylformamide were added N,N-diisopropylethylamine (3.49% mL), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo(4,5-b)pyridinium 3-oxide hexafluorophosphate (2.82 g) and 5-isopropylisoxazol-4-amine hydrochloride (1.15 g), and the mixture was stirred at room temperature for 48 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio) to give the title compound (2.50 g, 92%) as colorless amorphous crystals. MS: 405 (MH+).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0, volume ratio)

出典と根拠

ORDレコード
ord-349fb371c7ef4f34b310e206ee6671d9
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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