Hydroxylamine → HCID 54613496, compound

HRID 878467Notes

Reaction equation

HRID 878467 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](OC)=[O:16])=[N:8][C:4]=2[CH:3]=1.[NH2:21][OH:22].[OH-].[K+]>C1COCC1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:21][OH:22])=[O:16])[NH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 178500251HCID 178500251, compound

Product 1

HCID 54613496HCID 54613496, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 7-(5-bromo-1H-benzimidazol-2-yl)heptanoate (100 mg, 0.295 mmol) in THF at 0° C. was added 50% hydroxylamine solution (0.17 mL, 2.70 mmol). To this was added KOH (0.74 mL, 1M in MeOH, 0.74 mmol) dropwise. The reaction was stirred at 0° C. for 2 hr, briefly concentrated and neutralized by adding 1 N HCl solution until pH was 7. The light yellow precipitate was collected by filtration and pump-dried to give 7-(6-bromo-1H-benzimidazol-2-yl)-N-hydroxy heptanamide 15 (53 mg). The filtrate was extracted with ethyl acetate, dried and concentrated. The residue was purified by column to give another portion of the desired product 15 (16 mg). LCMS (M+1@retention time): [email protected] min (LC conditions: 1. Column: YMC, C-18 ODS, 50×4.6 mm 0.5 u; 2. Mobile phase: A 0.05% TFA in water and B 0.05% TFA in acetonitrile; 3. Flow rate 1.2 mL/min; Gradient program: 20% B to 100% B in 3 min).

Workup

  1. concentrationbriefly concentrated
  2. additionby adding 1 N HCl solution until pH was 7
  3. filtrationThe light yellow precipitate was collected by filtration
  4. custompump-dried

Sources & evidence

ORD record
ord-48a507cc83974632a6cfa7cfdfd79eef
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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