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

HRID 336220노트

반응식

HRID 336220 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-71e0d94af9a546b5a506860ac50e7d16
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889670B2

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