Hydrochloric Acid → (2R)-4-Biphenyl-4-yl-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533542ノート

反応式

HRID 533542 の反応式
Cl.[C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][O:14]C2CCCCO2)=[O:12])=[CH:4][CH:3]=1>CO>[C:2]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][OH:14])=[O:12])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86668767(2R)-4-Biphenyl-4-yl-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

生成物 1

HCID 51355576(2R)-4-Biphenyl-4-yl-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide収率 55%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of hydrochloric acid (4.2 mL, 4.0 M in 1,4-dioxane) was added to (2R)-4-biphenyl-4-yl-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (72 mg, 0.17 mmol). The reaction was allowed to stir at room temperature for 15 min, then anhydrous methanol (10 mL) was added. After 1 h, the reaction was concentrated under reduced pressure to provide a residue that was triturated with diethyl ether (35 mL). The ether was decanted off and the residual solvent was removed under reduced pressure to provide the title compound as an off-white solid (32 mg, 55%). LCMS m/z 348.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.62 (s, 3H), 2.09 (m, 1H), 2.45-2.56 (m, 2H), 2.65 (m, 1H), 2.96 (s, 3H), 7.21 (d, J=8.3 Hz, 2H), 7.25-7.29 (m, 1H), 7.34-7.39 (m, 2H), 7.46 (d, J=8.3 Hz, 2H), 7.49-7.52 (m, 2H).

後処理

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customto provide a residue that
  4. customwas triturated with diethyl ether (35 mL)
  5. customThe ether was decanted off
  6. customthe residual solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-178c3e78410a47828b419d63b8b1e135
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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