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

HRID 2374448

反応式

HRID 2374448 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-be0b16d5f18f4fc5b2a5e073d6350a0a
出典データセット
uspto-grants-2008_12
特許番号
US07462629B2

関連ノート

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