Acetic Acid → HCID 59423435, compound

HRID 1365022

Reaction equation

HRID 1365022 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH3:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[C:13]([OH:15])=[O:14].C(O)(=O)C.[B-]C#N.[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][CH:12]([C:11]([CH3:18])([CH3:17])[CH3:10])[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 108243-MethoxyanilineHCID 13150Trimethylpyruvic acidHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 59423435HCID 59423435, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-methoxyaniline (100 mg, 0.812 mmol) and trimethylpyruvic acid (211 mg, 1.624 mmol) in methanol (3 mL) at rt was added acetic acid (0.930 mL, 16.24 mmol). The mixture was stirred for 30 min at rt then heated at 70° C. for 2 hrs. The mixture was cooled down to rt before adding sodium cyanotrihydroborate (1.624 mL, 1.624 mmol). The mixture was stirred overnight at rt. Water (10 mL) was added, and the mixture was extracted with ethyl acetate (3×10 mL). The organic layer was washed with sat. NaHCO3 and brine solution, and then dried over Na2SO4, filtered, and evaporated to dryness. The residue was purified by preparative HPLC to get a white solid (30.5 mg, 16%) as product.

Workup

  1. temperaturethen heated at 70° C. for 2 hrs
  2. temperatureThe mixture was cooled down to rt
  3. stirringThe mixture was stirred overnight at rt
  4. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  5. washThe organic layer was washed with sat. NaHCO3 and brine solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8b2252f6b0b145209cd06fcde3d55936
Source dataset
uspto-grants-2011_02
Patent number
US07888464B2

Linked notes

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