Trifluoroacetic acid → 3-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester

HRID 2374448

반응식

HRID 2374448 반응식
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C.[C:47]([O:51][C:52](=[O:55])[CH:53]=[CH2:54])([CH3:50])([CH3:49])[CH3:48]>C(Cl)Cl>[C:47]([O:51][C:52](=[O:55])[CH2:53][CH2:54][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:29])([F:28])[F:30])[CH:21]=3)[CH:14]=2)[CH2:9]1)([CH3:50])([CH3:49])[CH3:48]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 15458tert-Butyl acrylateHCID 81531DiisopropylethylamineHCID 691462886-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

생성물 1

HCID 691740893-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (70 mg, 0.158 mmol) in CH2Cl2 (1 mL) is added TFA(1 mL). The mixture is stirred at room temperature for 30 minutes. All the solvents are removed under reduced pressure. The mixture is dissolved in CH3OH (1.5 mL). Then DIEA (269 μL, 10 eq.) and acrylic acid tert-butyl ester (46 μL, 2 eq.) are added. The mixture is heated to 90° C. for 20 minutes using microwave irradiation. All the solvent is evaporated and the mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient) to give 56 mg of 3-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester.

후처리

  1. customAll the solvents are removed under reduced pressure
  2. dissolutionThe mixture is dissolved in CH3OH (1.5 mL)
  3. temperatureThe mixture is heated to 90° C. for 20 minutes
  4. custommicrowave irradiation
  5. customAll the solvent is evaporated
  6. customthe mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient)

출처 및 근거

ORD 기록
ord-be0b16d5f18f4fc5b2a5e073d6350a0a
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462629B2

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