Terephthaloyl chloride → tert-butyl N-[(3S)-5-[4-[(3S)-3-(tert-butoxycarbonylamino)-2-oxo-3,4-dihydro-1H-1,5-benzodiazepine-5-carbonyl]benzoyl]-2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-3-yl]carbamate

HRID 1481937ノート

反応式

HRID 1481937 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.[C:28](Cl)(=[O:38])[C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>C1COCC1>[C:1]([O:5][C:6]([NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[N:10]([C:28]([C:29]2[CH:37]=[CH:36][C:32]([C:33]([N:23]3[C:24]4[CH:25]=[CH:18][CH:19]=[CH:11][C:12]=4[NH:13][C:14](=[O:15])[C@@H:27]([NH:7][C:6](=[O:20])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:26]3)=[O:34])=[CH:31][CH:30]=2)=[O:38])[CH2:9]1)=[O:20])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 7488Terephthaloyl chlorideHCID 8471TriethylamineHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate2 回

生成物 1

HCID 90220967tert-butyl N-[(3S)-5-[4-[(3S)-3-(tert-butoxycarbonylamino)-2-oxo-3,4-dihydro-1H-1,5-benzodiazepine-5-carbonyl]benzoyl]-2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-3-yl]carbamate収率 39%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (Intermediate 2) (57.9 mg, 0.209 mmol) and triethylamine (29.1 μL, 0.209 mmol) in anhydrous THF (1 mL) was added terephthaloyl dichloride (21.2 mg, 0.104 mmol). The resulting suspension was stirred at room temperature for 4 h. The mixture was concentrated and the residue was triturated with water. The solid was collected, washed with water and purified by silica gel chromatography to provide tert-butyl N-[(3S)-5-[4-[(3S)-3-(tert-butoxycarbonylamino)-2-oxo-3,4-dihydro-1H-1,5-benzodiazepine-5-carbonyl]benzoyl]-2-oxo-3,4-dihydro-1H-1,5-benzodiazepin-3-yl]carbamate as a white solid (27.6 mg, 39%).

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with water
  3. customThe solid was collected
  4. washwashed with water
  5. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-491a33b783d84fa9a97ab778b2b50ccd
出典データセット
uspto-grants-2016_08
特許番号
US09409888B2

反応ノート

読み込み中…