N-bromobutanimide → HCID 57816840, compound

HRID 2197465Notes

Reaction equation

HRID 2197465 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][CH:11]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[N:17][C:18]=2[NH2:22])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C1C(=O)N([Br:43])C(=O)C1>CC#N>[CH2:6]([O:5][P:4]([CH2:9][O:10][CH:11]([CH2:28][O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:12][N:13]1[C:21]([Br:43])=[N:20][C:19]2[C:14]1=[N:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[N:17][C:18]=2[NH2:22])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57816839HCID 57816839, compound

Product 1

HCID 57816840HCID 57816840, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the phosphonate prepared in step 2 (300 mg, 0.59 mmol) in CH3CN (5 ml) was added NBS (157 mg, 0.88 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The solvent was removed and the residue was washed with sat. aq Na2SO3 solution. The aqueous phase was extracted again with DCM. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by prep HPLC on a C18 column, eluting with a gradient of 5-95% CH3CN in H2O as solvent. 1H NMR (CDCl3) δ 1.19-1.27 (m, 6H), δ 3.40 (s, 3H), δ 3.68 (t, 2H), δ 3.84-3.3.88 (m, 1H), δ 3.93-4.10 (m, 8H), δ 4.30-4.36 (m, 4H), δ 6.30 (bs, 2H), δ 6.83-6.97 (m, 3H), δ 7.23-7.28 (m, 2H); MS: 588.2 (M+1).

Workup

  1. customThe solvent was removed
  2. washthe residue was washed with sat. aq Na2SO3 solution
  3. extractionThe aqueous phase was extracted again with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by prep HPLC on a C18 column
  8. washeluting with a gradient of 5-95% CH3CN in H2O as solvent

Sources & evidence

ORD record
ord-a8f078f816d7489e9a167f2d51a1655f
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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