Hydrochloric Acid → (R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl) pyridin-1(2H)-yl)butanamide

HRID 84312ノート

反応式

HRID 84312 の反応式
Cl.[CH3:2][C@@:3]([S:31]([CH3:34])(=[O:33])=[O:32])([CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:17]1=[O:30])[C:4]([NH:6][O:7]C1CCCCO1)=[O:5]>O1CCOCC1>[OH:7][NH:6][C:4](=[O:5])[C@:3]([CH3:2])([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:14][CH2:15][N:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][C:17]1=[O:30]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86671970(2R)-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl)pyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

生成物 1

HCID 57326985(R)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl) pyridin-1(2H)-yl)butanamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of 1.0 M aqueous HCl (10 ml) was added slowly to a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-(2-oxo-4-(phenylethynyl)pyridin-1(2H)-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (107 mg, 0.226 mmol) in 1,4-dioxane (20 mL) at room temperature. The reaction mixture was allowed to stir at room temperature overnight. After 18 hours the reaction was concentrated to low volume then redissolved in methanol (20 ml) and concentrated in vacuo to afford a light-yellow solid. Yield 71 mg, 81%. MS (APCI) m/z 389.4 (M+H), 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (none, 3 H) 1.53 (s, 3 H) 2.03-2.17 (m, 1 H) 2.33-2.45 (m, 1 H) 3.07 (s, 3 H) 3.71 (td, J=11.90, 4.88 Hz, 1 H) 3.96-4.14 (m, 1 H) 6.35 (dd, J=6.93, 1.85 Hz, 1 H) 6.56 (d, J=1.76 Hz, 1 H) 7.36-7.48 (m, 3 H) 7.51-7.61 (m, 2 H) 7.69 (d, J=7.02 Hz, 1 H) 11.05 (br. s., 1 H)

後処理

  1. concentrationAfter 18 hours the reaction was concentrated to low volume
  2. dissolutionthen redissolved in methanol (20 ml)
  3. concentrationconcentrated in vacuo
  4. customto afford a light-yellow solid

出典と根拠

ORDレコード
ord-abbcad299d694b31aa5a776431a97874
出典データセット
uspto-grants-2014_09
特許番号
US08846933B2

反応ノート

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