N-bromobutanimide → HCID 89995466, 화합물

HRID 1487296노트

반응식

HRID 1487296 반응식
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

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 89995465HCID 89995465, 화합물

생성물 1

HCID 89995466HCID 89995466, 화합물수율 52.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-308cf20127e840e4baae57ab25485dcb
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428511B2

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