Benzyl Alcohol → Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoate

HRID 248676

Reaction equation

HRID 248676 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([OH:15])=[O:14])=[O:8])(=[O:3])[CH3:2].[CH2:27](O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([S:4][CH2:5][CH:6]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([O:15][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:14])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 156701693-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoic acid

Product 1

HCID 15670183Benzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoateYield 64.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-[(2-Acetylthiomethyl-3-phenylpropionyl)amino]-4-methylbenzoic acid (compound of Example 21) (0.5 g), 4-dimethylaminopyridine (0.05 g), benzyl alcohol (0.17 g) and dichloromethane (20 ml) are mixed, and to the mixture is added EDC.HCl (0.27 g) with stirring under ice cooling, and the mixture is stirred at room temperature overnight. Dichloromethane is distilled off under reduced pressure, and the residue is dissolved in ethyl acetate, and the mixture is washed with 5% aqueous sodium hydrogen carbonate solution, 10% hydrochloric acid and saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate, and then ethyl acetate is distilled off under reduced pressure. The residue is dissolved in acetonitrile and purified by a medium pressure column chromatography with CHP-20P (eluent, water-acetonitrile). The fractions containing the desired compound are collected and the water and acetonitrile are distilled off under reduced pressure to give the title compound (0.40 g).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. distillationDichloromethane is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washthe mixture is washed with 5% aqueous sodium hydrogen carbonate solution, 10% hydrochloric acid and saturated aqueous sodium chloride solution in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationethyl acetate is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in acetonitrile
  8. custompurified by a medium pressure column chromatography with CHP-20P (eluent, water-acetonitrile)
  9. additionThe fractions containing the desired compound
  10. customare collected
  11. distillationthe water and acetonitrile are distilled off under reduced pressure

Sources & evidence

ORD record
ord-04f8b155c6b345cd88668864706a7983
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Linked notes

Loading…