Water → Carbonic acid 8-dimethylamino-1-methyl-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester

HRID 2367888노트

반응식

HRID 2367888 반응식
[CH3:1][N:2]([CH3:25])[N:3]1[CH2:24][CH2:23][C:6]2([N:10]([CH3:11])[C:9](=[O:12])[CH:8]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:7]2=[O:22])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35].O>O1CCCC1>[CH2:37]([O:36][C:34](=[O:35])[O:22][C:7]1[C:6]2([CH2:5][CH2:4][N:3]([N:2]([CH3:1])[CH3:25])[CH2:24][CH2:23]2)[N:10]([CH3:11])[C:9](=[O:12])[C:8]=1[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])[CH3:38]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 672263978-Dimethylamino-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione

생성물 1

HCID 67225510Carbonic acid 8-dimethylamino-1-methyl-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester수율 86.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

105 mg 8-Dimethylamino-1-methyl-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione (from Step 4) and 62 mg triethylamine are dissolved in 5 ml tetrahydrofuran, and the mixture cooled in an ice bath. Then, 40 mg ethyl chloroformate is added at 0° C. The mixture is allowed to warm to room temperature, and stirred for 2 hours. Then water is added and the mixture extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and the solvent evaporated. The crude product is purified by chromatography on silica gel, with acetone as a solvent, yielding 110 mg Carbonic acid 8-dimethylamino-1-methyl-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester as an oil. 1H-NMR (CDCl3): 6.85 ppm (s, 2H), 4.03 ppm (q, 2H), 3.00 ppm (m, 2H), 2.96 ppm (s, 3H), 2.85 ppm (m, 2H), 2.42 ppm (s, 6H), 2.27 ppm (m, 2H), 2.24 ppm (s, 3H), 2.16 ppm (s, 2H), 1.83 ppm (m, 2H), 1.09 ppm (t, 3H).

후처리

  1. temperaturethe mixture cooled in an ice bath
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe crude product is purified by chromatography on silica gel, with acetone as a solvent

출처 및 근거

ORD 기록
ord-9c258630ff854b779ada9233aa68fcbd
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703165B2

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