Triethylamine → HCID 21201786、化合物

HRID 1979451ノート

反応式

HRID 1979451 の反応式
N[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.C([N:27](CC)CC)C.[C:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]([CH:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[CH2:43][CH:42]([NH2:57])[C:41]2=[O:58])=[O:38])[S:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.C(Cl)(Cl)Cl.O>[C:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]([CH:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[CH2:43][CH:42]([NH:57][C:17]([NH:27][C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][CH:2]=3)=[O:23])[C:41]2=[O:58])=[O:38])[S:36][CH:35]=[CH:34][CH:33]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21201975HCID 21201975、化合物

生成物 1

HCID 21201786HCID 21201786、化合物収率 172.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
6.5 °C

実験手順

Ethyl 3-aminobenzoate (0.48 g) was dissolved in tetrahydrofuran (25 ml), the solution was cooled to internal temperature 5-8° C. Triphosgene (0.32 g) was added, and the mixture was stirred for 5 minutes. Subsequently, triethylamine (1.08 g) was added over 15 minutes interval. The resultant mixture was stirred at room temperature for 10 minutes,a solution of 1-(2-thenoylmethyl)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.99 g) in tetrahydrofuran (15 ml) was added and stirred for one hour. Water and chloroform were added to the reaction mixture and extracted. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, a mixed solvent of methylene chloride and ether (1:1) was added to crystals so precipitated for trituration, collected by filtration, to thereby obtain 1.07 g of the title compound.

後処理

  1. stirringstirred for one hour
  2. extractionextracted
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additiona mixed solvent of methylene chloride and ether (1:1) was added to crystals
  7. customso precipitated for trituration
  8. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-b926887e4f55464e8cca22737e11af14
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

読み込み中…