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 82857ノート

反応式

HRID 82857 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2f148f1807654e248729cd5dd330c8fa
出典データセット
uspto-grants-2014_09
特許番号
US08846741B2

反応ノート

読み込み中…