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

HRID 248676

反応式

HRID 248676 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-04f8b155c6b345cd88668864706a7983
出典データセット
uspto-grants-1993_05
特許番号
US05210266

関連ノート

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