Triethylamine → 1-[1-(thiophen-3-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

HRID 1979361ノート

反応式

HRID 1979361 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[S:32]1[CH:36]=[CH:35][C:34]([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[C:48]([CH3:51])[CH:49]=[CH:50][C:45]=3[N:44]([C:52](=[O:57])[C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:43][CH:42]([NH2:58])[C:41]2=[O:59])=[O:38])=[CH:33]1>O1CCCC1.O>[S:32]1[CH:36]=[CH:35][C:34]([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[C:48]([CH3:51])[CH:49]=[CH:50][C:45]=3[N:44]([C:52](=[O:57])[C:53]([CH3:54])([CH3:55])[CH3:56])[CH2:43][CH:42]([NH:58][C:14]([NH:1][C:2]3[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=3)=[O:16])[C:41]2=[O:59])=[O:38])=[CH:33]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 212016991-(thiophen-3-yl)carbonylmethyl-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 212018971-[1-(thiophen-3-yl)carbonylmethyl-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea収率 196.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ethyl 3-aminobenzoate (0.33 g) was dissolved in tetrahydrofuran (20 ml) and cooled on ice. Triphosgene (0.22 g) was added at internal temperature 5° C., triethylamine (0.76 g) was added dropwise thereto over 10 minutes period, the mixture was allowed to come to room temperature,stirred for 10 minutes. A solution of 1-(thiophen-3-yl)carbonylmethyl-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.69 g) in tetrahydrofuran (10 ml) was added, the resultant mixture was stirred for one hour. Water was added to the reaction mixture, extracted with methylene chloride, the organic layer was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=1:1), to thereby obtain 0.86 g of the titled compound as pale brown crystals (Yield: 75%).

後処理

  1. temperaturecooled on ice
  2. additionwas added dropwise
  3. customto come to room temperature
  4. extractionextracted with methylene chloride
  5. washthe organic layer was successively washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-001eb1a5d56e4ec5982c79f969e27148
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…