1,2-Dichloroethane → HCID 68921124、化合物

HRID 1785986ノート

反応式

HRID 1785986 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C@@H:15]([CH3:23])[CH2:14]2)[C:9](=[O:12])[CH2:10][OH:11])=[CH:4][CH:3]=1.C(Cl)CCl.[C:28](O)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([O:11][CH2:10][C:9]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C@@H:15]([CH3:23])[CH2:14]1)=[O:12])(=[O:30])[CH3:29]

参加物

5

反応物 3

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 68918824HCID 68918824、化合物

生成物 1

HCID 68921124HCID 68921124、化合物収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-(4-Chlorophenyl)-2-hydroxy-N-[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (300 mg, 0.91 mmol, 1 equ.) was dissolved in methylene chloride (3 mL). To this solution was added EDC (464 mg, 2.7 mmol, 3 equ.) and acetic acid (164 mg, 2.7 mmol, 3 equ.) and the reaction mixture was stirred at room temperature for 20 h. Reaction mixture was concentrated and the residue dissolved in ethyl acetate and washed with water, brine, and then dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (methylene chloride/methanol: 99/1 to 98/2 gradient) to afford 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (240 mg, 84%).

後処理

  1. customReaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (methylene chloride/methanol: 99/1 to 98/2 gradient)

出典と根拠

ORDレコード
ord-942d515f57e3447b811ce3444195e7b7
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

読み込み中…