Acetyl chloride → N-({8-Benzyl-7-[2,4-dioxo-3-azabicyclo[3.1.0]hex-3-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}methyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82857노트

반응식

HRID 82857 반응식
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:22])=[O:21])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:29][C:30]([C@H:32]1[CH2:34][C@H:33]1[C:35](O)=[O:36])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C>O1CCCC1.O>[CH2:1]([CH:8]1[C:17]2[CH:16]=[C:15]([CH2:18][NH:19][S:20]([C:23]3[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=3)(=[O:21])=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH:9]1[N:29]1[C:35](=[O:36])[CH:33]2[CH:32]([CH2:34]2)[C:30]1=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 6367Acetyl chlorideHCID 86685675cis-2-{[1-Benzyl-7-({[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}methyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid

생성물 1

HCID 86685674N-({8-Benzyl-7-[2,4-dioxo-3-azabicyclo[3.1.0]hex-3-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}methyl)-1-methyl-1H-imidazole-4-sulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

cis-2-{[1-Benzyl-7-({[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}methyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid (382 mg, 0.731 mmol) was dissolved in tetrahydrofuran (10 mL) and acetyl chloride (5 mL, 88 mmol) was added. The reaction mixture was heated under reflux for 2 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic extracts were washed with aqueous sodium bicarbonate solution, dried (sodium sulfate) and concentrated in vacuo. The crude product was used for the next step without further purificiation. Yield: 377 mg (light orange oil).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts were washed with aqueous sodium bicarbonate solution
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2f148f1807654e248729cd5dd330c8fa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846741B2

반응 노트

불러오는 중…