Sodium Iodide → HCID 86701268、化合物

HRID 2276069ノート

反応式

HRID 2276069 の反応式
[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]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 86701267HCID 86701267、化合物

生成物 1

HCID 86701268HCID 86701268、化合物収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-95b411e61bc342ac93ceab536d4f05b7
出典データセット
uspto-grants-2015_09
特許番号
US09131690B2

反応ノート

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