Borane → HCID 86701260、化合物

HRID 2276061ノート

反応式

HRID 2276061 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][O:16][C:15](=[O:18])[C@H:14]([CH2:19][C:20](O)=[O:21])[C@@H:13]([O:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[C@H:12]([CH3:29])[O:11][C:10]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:24]([O:23][C@@H:13]1[C@@H:14]([CH2:19][CH2:20][OH:21])[C:15](=[O:18])[O:16][CH2:17][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:10](=[O:30])[O:11][C@H:12]1[CH3:29])(=[O:28])[CH:25]([CH3:27])[CH3:26]

参加物

4

反応物 2

HCID 6331BoraneHCID 86701256HCID 86701256、化合物

生成物 1

HCID 86701260HCID 86701260、化合物収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

To a solution of 2-((3S,7R,8R,9S)-3-(tert-butoxycarbonylamino)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)acetic acid (2.0 g, 4.64 mmol) in THF (15 mL) was added borane (1.0 M in THF, 5.56 mL, 5.56 mmol) at 0° C. After 15 min the ice bath was removed and the reaction was allowed to warm to room temperature (about 22° C.). After an additional 1.5 h, the reaction was quenched with EtOAc (10 mL) and washed successively with 0.5 N HCl (10 mL) and sat'd aqueous NaHCO3 (10 mL). The phases were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (1.38 g, 72%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.40-5.19 (m, 2H), 5.07 (t, J=9.9 Hz, 1H), 4.95-4.75 (m, 2H), 3.74-3.52 (m, 3H), 2.83-2.68 (m, 1H), 2.61 (dt, J=13.9, 7.0 Hz, 1H), 2.07-1.90 (m, 1H), 1.70-1.52 (m, 1H), 1.44 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H); ESIMS m/z 440.3 ([M+Na]+).

後処理

  1. customAfter 15 min the ice bath was removed
  2. customthe reaction was quenched with EtOAc (10 mL)
  3. washwashed successively with 0.5 N HCl (10 mL)
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7cd347e9c76c4d57aea26531d1b3137d
出典データセット
uspto-grants-2015_09
特許番号
US09131690B2

反応ノート

読み込み中…