N-bromobutanimide → HCID 131723532, compound

HRID 989678Notes

Reaction equation

HRID 989678 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][C@@H:10]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:8][C:7]=2[CH:31]=1.[Br:32]N1C(=O)CCC1=O>CO.O>[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([Br:32])[C:6]2[N:12]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][C@@H:10]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:8][C:7]=2[CH:31]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 131723533HCID 131723533, compound

Product 1

HCID 131723532HCID 131723532, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the compound (200 mg) of Example 16 in methanol and water (7.5 mL/0.5 mL), was added N-bromosuccinimide (73 mg). The mixture was allowed to stir for 1 h, and solvent was removed. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to give a solid (90 mg, 35%). (M+H): 564.

Workup

  1. customsolvent was removed
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b6bf717f70d948458b275c6de1ffe6b6
Source dataset
uspto-grants-2002_10
Patent number
US06458783B1

Reaction notes

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