N-bromobutanimide → HCID 10216350, compound

HRID 1866884Notes

Reaction equation

HRID 1866884 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3](=[O:19])[O:4][C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[CH:6]=1.[Br:26]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3](=[O:19])[O:4][C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[C:6]=1[Br:26]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050484HCID 22050484, compound

Product 1

HCID 10216350HCID 10216350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-2-oxo-1,2-dihydropyridin-4-yl methyl(phenyl)carbamate (0.38 g, 1.13 mmol) in anhydrous CH2Cl2 (7 mL) was added N-Bromosuccinimide (NBS, 0.24 g, 1.34 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was purified by flash chromatography (silica gel) using EtOAc/hexanes (1:1 v/v). The appropriate fractions were collected according to ES MS (M+H 413) and concentrated. The dried product showed about 14% of di-brominated product by analytical HPLC. The compounds were separated by reverse phase HPLC using a 10-90% acetonitrile in water, 30 min gradient at a 100 mL/min flow rate, to afford (after lyophilization) the salt of the desired compound. The salt was diluted in EtOAc and washed with NaHCO3. The organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford the desired compound (0.271 g, 58%) as a beige solid.

Workup

  1. customThe reaction mixture was purified by flash chromatography (silica gel)
  2. customThe appropriate fractions were collected
  3. concentrationconcentrated
  4. customThe compounds were separated by reverse phase HPLC
  5. customa 10-90% acetonitrile in water, 30 min gradient

Sources & evidence

ORD record
ord-93410e31b9c8428a8f40821de4661060
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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