1-Bromo-3-methylbutane → HCID 60098544、化合物

HRID 1882916ノート

反応式

HRID 1882916 の反応式
Br[CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9](=[O:25])[C@H:10]([CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:15]([O:14][C:12]([NH:11][C@@H:10]([CH2:19][C:20]1[N:24]=[CH:23][N:22]([CH2:2][CH2:3][CH:4]([CH3:6])[CH3:5])[CH:21]=1)[C:9]([O:8][CH3:7])=[O:25])=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 78911-Bromo-3-methylbutaneHCID 10340Sodium CarbonateHCID 178501431HCID 178501431、化合物

生成物 1

HCID 60098544HCID 60098544、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-Bromo-3-methylbutane (4.44 ml, 37.2 mmol) was added to a mixture of Nα-Boc-L-histidine methyl ester (5.0 g, 18.6 mmol) and sodium carbonate (4.0 g, 37.2 mmol) in acetonitrile (80 ml), and the mixture was heated under reflux for 18 hours. The cooled mixture was concentrated under reduced pressure. The residue was suspended in water and the suspension was basified using sodium carbonate then extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried (Na2SO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95) to afford the title compound as a colourless oil, 2.8 g. 1H-NMR (CDCl3, 400 MHz) δ: 0.90 (d, 6H), 1.40 (s, 9H), 1.50 (m, 1H), 1.60 (m, 2H), 2.96-3.06 (m, 2H), 3.62 (s, 3H), 3.82 (t, 2H), 4.50 (m, 1H), 5.85 (m, 1H), 6.62 (s, 1H), 7.32 (s, 1H). LRMS: m/z (ES+) 340 [MH+]. [α]D=−2.3 (c=0.22, methanol).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. extractionthen extracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe residual oil was purified by column chromatography on silica gel using an elution gradient of hexane:ethyl acetate (100:0 to 5:95)

出典と根拠

ORDレコード
ord-b0d851b38c1a4047b8ad4f6065e8e457
出典データセット
uspto-grants-2004_07
特許番号
US06759426B2

反応ノート

読み込み中…