Imidazole → (S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191513노트

반응식

HRID 1191513 반응식
O[CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>C(Cl)(Cl)Cl>[I:41][CH2:2][C@@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68915929(S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

생성물 1

HCID 68912224(S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one수율 80%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A reaction flask was charged with (S)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (2.52 g, 11.4 mmol), triphenylphosphine (6.12 g, 23.3 mmol), imidazole (1.98 g, 29.1 mmol), and iodine (8.88 g, 35.0 mmol) in CHCl3 (30 mL) and stirred at rt for 20 h. The reaction mixture was washed with saturated sodium thiosulfate, dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 3:1) to give the title compound (3.02 g, 80%). 1H NMR (CDCl3) δ 7.07-7.00 (m, 4H), 4.65-4.55 (m, 2H), 3.94 (dd, J=1.7 Hz, J=6.7 Hz, CH2), 3.23-3.14 (m, 2H), 2.18-2.07 (m, 1H), 1.05 (d, J=6.1 Hz, CH3).

후처리

  1. washThe reaction mixture was washed with saturated sodium thiosulfate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 3:1)

출처 및 근거

ORD 기록
ord-f979c15a631d4e528d6cc06a3fe2c23c
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680115B2

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