Ammonium Acetate → HCID 59506112, compound

HRID 1098745Notes

Reaction equation

HRID 1098745 reaction equation
C([O-])(=O)C.[NH4+].[CH3:6][O:7][CH2:8][CH2:9][N:10]([CH3:24])[C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH3:18])=[CH:13][C:12]=1[C:20]([F:23])([F:22])[F:21].C([BH3-])#[N:26].[Na+]>CO>[NH2:26][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([N:10]([CH2:9][CH2:8][O:7][CH3:6])[CH3:24])=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:13]=1)[CH3:18]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 59506298HCID 59506298, compound

Product 1

HCID 59506112HCID 59506112, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonium acetate (1.53 g, 19.8 mmol) was added to a solution of the compound from step 1 (545 mg, 1.98 mmol) in MeOH (8 mL). After stirring at RT overnight sodium cyanoborohydride (149 mg, 2.38 mmol) was added and the reaction was refluxed for 6 h. The solvent was evaporated and the solid, redissolved in ethyl acetate, was extracted with water. The organic layer was separated, washed with brine, dried over sodium sulphate, filtered, evaporated and purified by preparative HPLC. The relevant fractions were lyophilized to give 147 mg (yield: 19%) of the pure product.

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed for 6 h
  3. customThe solvent was evaporated
  4. dissolutionthe solid, redissolved in ethyl acetate
  5. extractionwas extracted with water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-04c75462cdcf49ef9ebf3ef5575adfa2
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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