Benzoyl chloride → (S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

HRID 1374555노트

반응식

HRID 1374555 반응식
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57617767(S)-tert-Butyl (1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)carbamate

생성물 1

HCID 69508172(S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-(1-Methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (260 mg, 0.55 mmol), triethylamine (111 mg, 1.1 mmol), and benzoyl chloride (93 mg, 0.66 mmol) were dissolved in dichloromethane (2 ml) and stirred overnight. The reaction mixture was then poured on HCl (1N), and extracted with dichloromethane. The organic layer was washed with NaHCO3 (1N), dried, and evaporated. (S)-(5-Benzoyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester was obtained in sufficient purity for the next step.

후처리

  1. additionThe reaction mixture was then poured on HCl (1N)
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with NaHCO3 (1N)
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-a71a1d4fc5954837b76049576ba30331
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166587B2

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