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Triethylamine → 5-chloro-N-(Trans-2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide

HRID 2240851
ノート
印刷プレビュー

反応式

HRID 2240851 の反応式
[CH3:1][C:2]1([CH3:12])[C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[NH2:11].C(N(CC)CC)C.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26](O)=[O:27].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25]([CH:29]=1)[C:26]([NH:11][C@H:3]1[C@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1([CH3:12])[CH3:1])=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68583334trans-2,2-Dimethyl-3-phenyl-cyclopropylamine

生成物 1

HCID 576527575-chloro-N-(Trans-2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of trans-2,2-dimethyl-3-phenyl-cyclopropylamine (1.04 g, 6.5 mmol) in DCM was added triethylamine (1.435 g, 14.3 mmol), followed by 5-chloro-2-methoxybenzoic acid (1.446 g, 7.44 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (2.696 g, 8.45 mmol). The resulting mixture was stirred at room temperature overnight, then poured into water and extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (0% to 15% of EtOAc in hexane) to give 1.71 g (86% yield) of trans-5-chloro-N-(2,2-dimethyl-3-phenyl-cyclopropyl)-2-methoxy-benzamide, MS=330 [M+H]+.

後処理

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (0% to 15% of EtOAc in hexane)

出典と根拠

ORDレコード
ord-54420dd2c7a14706af85b64cb95479a4
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07723391B2

反応ノート

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