Methanol → (R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

HRID 445279

반응식

HRID 445279 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:30]([O:33][C:34]([C:37](Cl)=[O:38])([CH3:36])[CH3:35])(=[O:32])[CH3:31].CO>C(Cl)Cl>[C:30]([O:33][C:34]([CH3:36])([CH3:35])[C:37](=[O:38])[N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)(=[O:32])[CH3:31]

참가 물질

6

반응물 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 1234962-Acetoxyisobutyroyl chloride2회HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 59536313(R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (207 mg, 747 μmol, example 30 (step 1) and DIEA (130 μL, 747 μmol) in DCM (2.5 mL) was added 1-chlorocarbonyl-1-methylethyl acetate (119 μL, 821 μmol). The mixture was stirred at RT for 3 h. Then, 1-chlorocarbonyl-1-methylethyl acetate (50 μL) was added and the mixture was stirred at RT for 16 h. MeOH (1 mL) was added and the mixture was filtered. The filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA) to give the title compound in a solution of H2O 0.1% TFA and MeCN 0.1% TFA. The solvent was removed and saturated NaHCO3 (5 mL) was added. The mixture was extracted with EtOAc (2×30 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give the title compound as a white solid. MS (ESI, positive ion) m/z: 406 (M+H).

후처리

  1. stirringthe mixture was stirred at RT for 16 h
  2. filtrationthe mixture was filtered
  3. customThe filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA)

출처 및 근거

ORD 기록
ord-1788a70662394664921c8942a9e49528
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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