p-Bromochlorobenzene → (S)-1-(4-Chloro-phenyl)-azepane-2-carboxylic acid

HRID 336220ノート

反応式

HRID 336220 の反応式
Cl.C(C1ON=C(N[C:12]([C@@H:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)=[O:13])C=1)(C)(C)C.Br[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-:30].[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O.[Cu]I>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:14]2[C:12]([OH:13])=[O:30])=[CH:23][CH:24]=1

参加物

7

反応物 3

HCID 7806p-BromochlorobenzeneHCID 11430Potassium CarbonateHCID 86660403(S)-Perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride

生成物 1

HCID 58563924(S)-1-(4-Chloro-phenyl)-azepane-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of (S)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride (prepared according to Method T, step 6) (0.60 g, 4.20 mmol), 1-Bromo-4-chloro-benzene (0.80 g, 4.20 mmol), potassium carbonate (0.87 g, 6.29 mmol) and copper (I) iodide (0.08 g, 0.42 mmol) in DMA (10.0 mL), is heated at 100° C. in a sealed tube for 48 hours. The reaction mixture is diluted with EtOAc and washed with water. The water phase is acidified with 1N HCl and then extracted with EtOAc. The organic layers are combined, and after drying over anhydrous Na2SO4, removal of the solvent affords the title product that is used in the next step without any further purification. m/z 254 [M+H].

後処理

  1. washwashed with water
  2. extractionextracted with EtOAc
  3. dry with materialafter drying over anhydrous Na2SO4, removal of the solvent

出典と根拠

ORDレコード
ord-71e0d94af9a546b5a506860ac50e7d16
出典データセット
uspto-grants-2014_11
特許番号
US08889670B2

反応ノート

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