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Acetamide → N-Acetyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetamide

HRID 1975722
ノート
印刷プレビュー

反応式

HRID 1975722 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:20](O)=[O:21])=[CH:15][CH:14]=1.C(N(CC)CC)C.S(Cl)(C)(=O)=O.[C:42]([NH2:45])(=[O:44])[CH3:43].CN(C1C=CC=CN=1)C>C1COCC1>[C:42]([NH:45][C:20](=[O:21])[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:14][CH:15]=1)[CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)(=[O:44])[CH3:43]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 178AcetamideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 113267232-Cycloheptyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-acetic acid

生成物 1

HCID 9824020N-Acetyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetamide

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

8.0 g (0.02 mol) of 2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cycloheptyl-acetic acid and 4.0 g (5.6 ml/0.04 mol) of triethylamine are dissolved in 80 ml of THF, the solution is cooled to 0° C., and 2.3 g (1.6 ml/0.02 mol) of mesyl chloride are added. 2.4 g (0.04 mol) of acetamide and 7.2 g (0.06 mol) of dimethylaminopyridine (DMAP), dissolved in 20 ml of THF, are added at 0° C. The mixture is allowed to react at room temperature for 48 hours (stirring) and is then concentrated to dryness in vacuo, and the residue is extracted by stirring with 50 ml of water and 50 ml of dichloromethane. The organic phase is separated off, dried and concentrated to a small volume, and the residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate/ glacial acetic acid=8/1/1).

後処理

  1. additionare added at 0° C
  2. customto react at room temperature for 48 hours
  3. concentrationis then concentrated to dryness in vacuo
  4. extractionthe residue is extracted
  5. stirringby stirring with 50 ml of water and 50 ml of dichloromethane
  6. customThe organic phase is separated off
  7. customdried
  8. concentrationconcentrated to a small volume
  9. customthe residue is separated by column chromatography (silica gel 60, mobile phase: toluene/ethyl acetate/ glacial acetic acid=8/1/1)

出典と根拠

ORDレコード
ord-f1fa6553909348bd96d6ab4e36286eae
出典データセット
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05288733

反応ノート

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