N-bromobutanimide → HCID 89995466, compound

HRID 1487296Notes

Reaction equation

HRID 1487296 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 89995466HCID 89995466, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-308cf20127e840e4baae57ab25485dcb
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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