Hydroxylamine → HCID 44182588, compound

HRID 878472Notes

Reaction equation

HRID 878472 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](OC)=[O:22])[NH:12][C:11]=3[CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][OH:27].[OH-].[K+]>C1COCC1>[OH:27][NH:26][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:13]1[NH:12][C:11]2[CH:25]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=[CH:9][C:10]=2[N:14]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 66778756HCID 66778756, compound

Product 1

HCID 44182588HCID 44182588, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanoate (50 mg, 0.15 mmol) in THF at 0° C. was added 50% hydroxylamine solution (0.10 mL, 1.5 mmol). To this was added KOH (0.45 mL, 1M in MeOH, 0.45 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 white precipitate was collected by filtration and purified by biotage column chromatography to give N-hydroxy-7-(6-phenyl-1H-benzo[d]imidazol-2-yl)heptanamide 18 (27 mg). MS (M+1=338)

Workup

  1. concentrationbriefly concentrated
  2. additionby adding 1 N HCl solution until pH was 7
  3. filtrationThe white precipitate was collected by filtration
  4. custompurified by biotage column chromatography

Sources & evidence

ORD record
ord-59d227f1e5ad4fcb9f836ade697e9740
Source dataset
uspto-grants-2015_03
Patent number
US08987468B2

Reaction notes

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