Triethylamine → (R)-(-)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea

HRID 1979466ノート

反応式

HRID 1979466 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(N(CC)CC)C.[O:34]=[C:35]1[NH:41][C:40]2[CH:42]=[CH:43][CH:44]=[CH:45][C:39]=2[N:38]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:37][C@H:36]1[NH2:52]>O1CCCC1>[O:34]=[C:35]1[NH:41][C:40]2[CH:42]=[CH:43][CH:44]=[CH:45][C:39]=2[N:38]([CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:37][C@H:36]1[NH:52][C:5]([NH:13][C:14]1[CH:26]=[CH:25][CH:24]=[C:16]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH:15]=1)=[O:11]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 2737408tert-Butyl-3-aminobenzoateHCID 54463364(R)-(-)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 54084555(R)-(-)-1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-tert-butoxycarbonylphenyl)urea収率 254.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphosgene (1.8 g) was added to a solution of tert-butyl 3-aminobenzoate (3.13 g) in anhydrous tetrahydrofuran (200 ml) under ice-cooling, and then triethylamine (7.25 ml) was added five times each 1.45 ml over 15 minutes, and the mixture was stirred at room temperature for 5 minutes. Subsequently (R)-(−)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (4 g) was added under ice-cooling. The mixture was stirred at room temperature for one hour, the reaction mixture was concentrated under reduced pressure. Ice-water was added to the residue, extracted with methylene chloride,the organic layer was washed with saturated brine. After dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue, crystals were collected by filtration, to thereby obtain 7.38 g of the titled compound.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for one hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionIce-water was added to the residue
  6. extractionextracted with methylene chloride,the organic layer
  7. washwas washed with saturated brine
  8. dry with materialAfter dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionDiisopropyl ether was added to the residue, crystals
  11. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-5a8a17b9b5ae4c708cfdaf91daa6492d
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

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