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Water → 4-(4-chlorobenzyl)-2-[5-(N-methyl-N-benzylamino)-1-carboxy-t-butyl-3-pentyl]-1(2H)-phthalazinone

HRID 128700
ノート
印刷プレビュー

反応式

HRID 128700 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][N:10]=2)=[CH:6][CH:5]=1.C([O:26][C:27](=[O:47])[CH2:28][CH2:29][CH:30](OS(C)(=O)=O)[CH2:31][CH2:32][N:33]([CH3:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(C)(C)C.O>CC(N(C)C)=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[N:11]([CH:30]([CH2:31][CH2:32][N:33]([CH3:41])[CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:29][CH:28]([C:7]([CH3:20])([CH3:8])[CH3:6])[C:27]([OH:26])=[O:47])[N:10]=2)=[CH:20][CH:21]=1
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

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1044524-(4-chlorobenzyl)phthalazin-1(2H)-oneHCID 193747646-(N-methyl-N-benzylamino)-4-methylsulfonyloxy-caproic acid-t-butyl ester

生成物 1

HCID 677840344-(4-chlorobenzyl)-2-[5-(N-methyl-N-benzylamino)-1-carboxy-t-butyl-3-pentyl]-1(2H)-phthalazinone

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒
2 回

反応条件

温度
50 °C

実験手順

3 g sodium hydride (80%, in white oil) are added to 21.6 g 4(4-chlorobenzyl)-1(2H)-phthalazinone in 200 ml dimethylacetamide (DMA) with cooling in an ice bath. 37 g 6-(N-methyl -N-benzylamino )-4-methylsulfonyloxy-caproic acid-t-butyl ester in 80 ml DMA are then added dropwise with cooling and stirring continued for 0.5 hour. The mixture is allowed to warm slowly--overnight--to room temperature and is then heated for 2 hours to 40° C.-50° C. The mixture is hydrolyzed by addition of 200 ml water with ice cooling. The precipitated oil is separated and dissolved in dichloromethane. After extraction twice with water, the organic phase is dried and concentrated. The residue is chromatographed over silica gel (Eluent: dichloromethane/methanol/ammonia 25% 95:4:1). 3.5 g are obtained (yellow oil).

後処理

  1. temperaturewith cooling in an ice bath
  2. temperaturewith cooling
  3. temperatureto warm slowly
  4. customThe precipitated oil is separated
  5. dissolutiondissolved in dichloromethane
  6. extractionAfter extraction twice with water
  7. customthe organic phase is dried
  8. concentrationconcentrated
  9. customThe residue is chromatographed over silica gel (Eluent: dichloromethane/methanol/ammonia 25% 95:4:1)
  10. custom3.5 g are obtained (yellow oil)

出典と根拠

ORDレコード
ord-a3a73084e2704186848bc4e2057b0830
出典データセット
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05464838

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート