Sodium Iodide → HCID 86701268, 화합물

HRID 2276069노트

반응식

HRID 2276069 반응식
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17]OS(C)(=O)=O)[C:14](=[O:23])[O:13][CH2:12][C@H:11]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:10](=[O:32])[O:9][C@H:8]1[CH3:33])(=[O:5])[CH:2]([CH3:4])[CH3:3].[Na+].[I-:35]>CN(C=O)C>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][I:35])[C:14](=[O:23])[O:13][CH2:12][C@H:11]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:10](=[O:32])[O:9][C@H:8]1[CH3:33])(=[O:5])[CH:2]([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 86701267HCID 86701267, 화합물

생성물 1

HCID 86701268HCID 86701268, 화합물수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-6-methyl-8-(2(methylsulfonyloxy)ethyl)-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (350 mg, 0.71 mmol) in DMF (3 mL) at room temperature (about 22° C.) was added NaI (1.06 g, 7.06 mmol), and the resulting reaction mixture was heated to 60° C. and stirred for 6 h. The reaction mixture was partitioned between sat'd aqueous NaHCO3 solution (20 mL) and EtOAc (25 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2×25 mL) and the combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated to dryness. The crude residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (300 mg, 81%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 5.43-5.15 (m, 2H), 5.07 (t, J=9.8 Hz, 1H), 4.95-4.75 (m, 2H), 3.72-3.51 (m, 1H), 3.24 (ddd, J=10.6, 6.6, 4.3 Hz, 1H), 3.00-2.87 (m, 1H), 2.82 (td, J=10.9, 3.0 Hz, 1H), 2.62 (hept, J=7.0 Hz, 1H), 2.35-2.21 (m, 1H), 1.86-1.69 (m, 1H), 1.45 (s, 9H), 1.28 (d, J=6.3 Hz, 3H), 1.22 (dd, J=7.0, 3.9 Hz, 6H); ESIMS m/z 550 ([M+Na]+).

후처리

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was partitioned between sat'd aqueous NaHCO3 solution (20 mL) and EtOAc (25 mL)
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with EtOAc (2×25 mL)
  5. dry with materialthe combined EtOAc extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient)

출처 및 근거

ORD 기록
ord-95b411e61bc342ac93ceab536d4f05b7
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09131690B2

반응 노트

불러오는 중…