Ethyl Acetate → HCID 67611902, compound

HRID 580886Notes

Reaction equation

HRID 580886 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:22]([C:24]1[CH:37]=[CH:36][C:27]([CH2:28][N:29]2[C:33]([CH:34]=O)=[CH:32][N:31]=[CH:30]2)=[CH:26][CH:25]=1)#[N:23].CCOC(C)=O>ClCCCl>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:29]2[C:33]([CH2:34][NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[CH:32][N:31]=[CH:30]2)=[CH:36][CH:37]=1)#[N:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 122755Glycine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Product 1

HCID 67611902HCID 67611902, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of glycine methyl ester hydrochloride (595 mg, 4.74 mmol) in 1,2-dichloroethane at 0° C. was added 4 Å powdered molecular sieves (3 g), followed by sodium triacetoxyborohydride (1.51 g, 7.1 mmol). The 1-(4-cyanobenzyl)-5-imidazolecarboxaldehyde from Step E of Example 1 (1.00 g, 4.74 mmol) was added, and the reaction was stirred overnight, allowing it to warm to room temperature. The reaction was poured into EtOAc, washed with sat. aq. NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was taken up in CH2Cl2, and propylamine (20 vol %) was added. The reaction was stirred for one hour, then concentrated in vacuo, and purified by silica gel chromatography (95:5; CHCl3:MeOH) to provide the titled amine product.

Workup

  1. washwashed with sat. aq. NaHCO3, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionpropylamine (20 vol %) was added
  6. stirringThe reaction was stirred for one hour
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel chromatography (95:5; CHCl3:MeOH)

Sources & evidence

ORD record
ord-2f87a091cad0408c96f7337b7a50352b
Source dataset
uspto-grants-1999_07
Patent number
US05919785

Reaction notes

Loading…