N-bromobutanimide → HCID 89995466、化合物

HRID 1487296ノート

反応式

HRID 1487296 の反応式
C1C(=O)N([Br:8])C(=O)C1.[C:9]([O:13][C:14]([NH:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:8][C:20]1[N:19]=[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:17]([NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH:21]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 89995465HCID 89995465、化合物

生成物 1

HCID 89995466HCID 89995466、化合物収率 52.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of NBS (1.548 g, 8.70 mmol) in DMF (15 ml) was added slowly via addition funnel to a solution of ethyl 1-((tert-butoxycarbonyl)amino)-1H-imidazole-2-carboxylate (2.22 g, 8.70 mmol) in DMF (12 ml) at room temperature. The reaction was stirred at room temperature overnight. To the reaction was added a saturated solution of sodium bicarbonate until the yellow solution became a white suspension. The mixture was concentrated to dryness. The residue was partitioned between EtOAc and water. The organic phase was washed (brine), dried (Na2SO4) and concentrated to give a yellow viscous oil. The crude product was purified via silica gel column (Isco prep: 15-100% ethyl acetate/hexanes) to afford ethyl 4-bromo-1-((tert-butoxycarbonyl)amino)-1H-imidazole-2-carboxylate (1.52 g, 4.55 mmol, 52.3% yield) as a white solid. LCMS (Method B) m/z 334.1 [M+1], Br-pattern; 1H NMR (400 MHz, chloroform-d) δ 7.26 (s, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.51 (s, 9H), 1.42 (t, J=7.2 Hz, 3H).

後処理

  1. concentrationThe mixture was concentrated to dryness
  2. customThe residue was partitioned between EtOAc and water
  3. washThe organic phase was washed (brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a yellow viscous oil
  7. customThe crude product was purified via silica gel column (Isco prep: 15-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-308cf20127e840e4baae57ab25485dcb
出典データセット
uspto-grants-2016_08
特許番号
US09428511B2

反応ノート

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