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Potassium Carbonate → Methyl 3-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

HRID 1751125
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HRID 1751125 반응식
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+].I[CH2:35][CH2:36][CH2:37][C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39]>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:35][CH2:36][CH2:37][C:38](=[O:39])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:10][CH2:11]2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:4][N:3]1[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22]
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6

반응물 3

HCID 11430Potassium CarbonateHCID 110869514-Iodo-1-phenylbutan-1-oneHCID 66652446Methyl 3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

생성물 1

HCID 58046782Methyl 3-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate수율 65.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
55 °C

실험 절차

To a solution of methyl 3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate (0.12 g, 0.33 mmol) and potassium carbonate (0.091 g, 0.66 mmol) in N,N-dimethylformamide (3 mL), was added 4-iodo-1-phenylbutan-1-one (0.09 g, 0.33 mmol). After stirring at 55° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (50 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, and isolated by Biotage flash chromatography (1-8% methanol/dichloromethane) to obtain the title compound (0.11 g, 65%); 1H NMR (DMSO-d6): δ 1.75 (d, 2H, J=10.8 Hz), 1.83 (t, 2H, J=7.2 Hz), 2.35-2.41 (m, 4H), 2.67-2.74 (m, 4H), 3.04 (t, 2H, J=7.2 Hz), 3.88 (s, 3H), 5.19 (s, 2H), 6.87 (t, 1H, J=7.6 Hz), 7.02 (d, 2H, J=8 Hz), 7.24 (t, 2H, J=8.4 Hz), 7.52 (t, 2H, J=7.2 Hz), 7.57-7.65 (m, 2H), 7.79 (dt, 1H, J=8 and 1.2 Hz), 7.90-7.99 (m, 3H), 8.58 (t, 1H, J=1.6 Hz); MS for C31H33N3O4 m/z 512.3 (M+H)+.

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customisolated by Biotage flash chromatography (1-8% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-6bdec9d8dc3e43feba5ec6ffe2604f92
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09156840B2

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