Cyanogen Bromide → HCID 11248809, compound

HRID 1866861Notes

Reaction equation

HRID 1866861 reaction equation
C(=O)(O)[O-].[Na+].[C:6]1([C:12]2([C:19]3[CH:28]=[C:27]([O:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)[CH:26]=[CH:25][C:20]=3[C:21]([NH:23][NH2:24])=[O:22])[CH2:17][CH:16]3[CH2:18][CH:13]2[CH2:14][CH2:15]3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:41]#[C:42]Br>O.O1CCOCC1>[C:6]1([C:12]2([C:19]3[CH:28]=[C:27]([O:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)[CH:26]=[CH:25][C:20]=3[C:21]3[O:22][C:42]([NH2:41])=[N:24][N:23]=3)[CH2:17][CH:16]3[CH2:18][CH:13]2[CH2:14][CH2:15]3)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium Bicarbonate2×HCID 57978651HCID 57978651, compound

Product 1

HCID 11248809HCID 11248809, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of sodium bicarbonate (10.0 mg, 0.12 mmol) in water (267 μL) was added dropwise via syringe to a stirred solution of 4d (0.108 mmol) in dioxane (1.0 mL) at room temperature. A suspension of cyanogen bromide (13.0 mg, 0.12 mmol) in dioxane (120 μL) was added in 4 equal portions at 1 minute intervals. After approximately 45 min, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 0-75% acetonitrile/water as eluent, 0.1% TiFA as modifier). Lyophilization of the purified fractions afforded the title compound 5b, m/z (ES) 489 (MH)+.

Workup

  1. additionwas added in 4 equal portions at 1 minute intervals
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 0-75% acetonitrile/water as eluent, 0.1% TiFA as modifier)

Sources & evidence

ORD record
ord-fc8d250865794ca79ddc3586c1eafbec
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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