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 1481937노트

반응식

HRID 1481937 반응식
[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]

참가 물질

5

반응물 3

HCID 7488Terephthaloyl chlorideHCID 8471TriethylamineHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate2회

생성물 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]carbamate수율 39%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-491a33b783d84fa9a97ab778b2b50ccd
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409888B2

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