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

HRID 533542노트

반응식

HRID 533542 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-178c3e78410a47828b419d63b8b1e135
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853258B2

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