Phosgene → 5-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

HRID 427666ノート

反応式

HRID 427666 の反応式
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])=[C:13]([CH:15]=1)[NH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27](Cl)(Cl)=[O:28].[N:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([CH2:43][OH:44])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:16]2[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]2=[O:21])=[C:13]([CH:15]=1)[NH:14][C:27]([O:44][CH2:43][CH:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)[CH2:42][CH2:41]1)=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 6371PhosgeneHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanolHCID 181744945-(Tert-butyldimethylsilyloxy)-2-phthalimidoaniline

生成物 1

HCID 181745295-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline収率 90%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

A solution of 5-(tert-butyldimethylsilyloxy)-2-phthalimidoaniline (1.02 g, 2.77 mmol) in toluene (15 mL) was treated with a solution of 20% phosgene in toluene (2 mL) at reflux for 20 min. The volatile materials were removed in vacuo to give a tan solid, which was dissolved in dry methylene chloride (20 mL) and treated with 1-(4-pyridyl)piperidine-4-methanol (0.53 g, 2.77 mmol). The resulting suspension was stirred for 90 min then diluted with hexane. The mixture was allowed to stand overnight and the resulting precipitate collected by vacuum filtration and dried to yield 1.46g (90%) of the title compound as a tan powder.

後処理

  1. temperatureat reflux for 20 min
  2. customThe volatile materials were removed in vacuo
  3. customto give a tan solid, which
  4. waitto stand overnight
  5. filtrationthe resulting precipitate collected by vacuum filtration
  6. customdried

出典と根拠

ORDレコード
ord-3a0241fc12ef445383c48e33e9ce0cda
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

反応ノート

読み込み中…