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

HRID 248676

반응식

HRID 248676 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-04f8b155c6b345cd88668864706a7983
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210266

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