Acetic Acid → HCID 57251616, compound

HRID 1699050Notes

Reaction equation

HRID 1699050 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([CH2:23][CH2:24][CH2:25][NH2:26])=[CH:21][CH:22]=1)=[O:17].[O-]S([O-])(=O)=O.[Na+].[Na+].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.CCOC(C)=O>[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([CH2:23][CH2:24][CH2:25][NH:26][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=2)=[CH:21][CH:22]=1)=[O:17]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 24436Sodium Sulfate2×HCID 709884-ButylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69544452HCID 69544452, compound

Product 1

HCID 57251616HCID 57251616, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-butylbenzaldehyde (250 mg, 1.541 mmol), 5-(3-amino-propyl)-thiophene-2-carboxylic acid methyl ester hydrochloride (403 mg, 1.695 mmol), and Na2SO4 (2.189 g, 15.41 mmol) in MeOH (10 mL) was heated at reflux for 4.5 h and additional Na2SO4 (2.19 g) was added. The reaction was heated at reflux for 1 h and was cooled to room temperature. The solids were filtered off with the aid of MeOH and the volatiles were removed in vacuo. The residue was dissolved in THF (10 mL) and CH2Cl2 (10 mL) and the solution was cooled to 0° C. Acetic acid (185 mg, 3.082 mmol) was added followed by sodium triacetoxyborohydride (653 mg, 3.082 mmol) and the reaction was stirred at room temperature for 16 h. The reaction was diluted with EtOAc and the organic solution was washed with aqueous NaHCO3 followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (99:1 CHCl3:MeOH to 97.5:2.5 CHCl3:MeOH) provided the title compound (309 mg). MS 346 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 h
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 1 h
  5. filtrationThe solids were filtered off with the aid of MeOH
  6. customthe volatiles were removed in vacuo
  7. dissolutionThe residue was dissolved in THF (10 mL)
  8. temperatureCH2Cl2 (10 mL) and the solution was cooled to 0° C
  9. washthe organic solution was washed with aqueous NaHCO3
  10. dry with materialThe organic solution was dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customPurification by flash chromatography (99:1 CHCl3:MeOH to 97.5:2.5 CHCl3:MeOH)

Sources & evidence

ORD record
ord-5a350b719bf2416abc70404e53bd58c3
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

Loading…