tert-Butyl cyanoacetate → HCID 22258721, 화합물

HRID 1611173노트

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HRID 1611173 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[C:23](=O)[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]([CH:28]1[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]1)=O.[C:41]([O:45][C:46](=[O:50])[CH2:47][C:48]#[N:49])([CH3:44])([CH3:43])[CH3:42].C([O-])(=O)C.[NH4+:55]>COCCOC>[NH2:49][C:48]1[N:55]=[C:23]([C:10]2[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=[CH:12][C:11]=2[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:24]=[C:26]([CH:28]2[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]2)[C:47]=1[C:46]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:50]

참가 물질

6

반응물 4

HCID 70693tert-Butyl cyanoacetateHCID 517165Ammonium AcetateHCID 8388661-[2,6-bis(benzyloxy)phenyl]ethanone2회HCID 99644481-Boc-piperidine-3-carboxaldehyde2회

생성물 1

HCID 22258721HCID 22258721, 화합물수율 16%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

A mixture of 1-[2,6-bis(benzyloxy)phenyl]ethanone (8.00 g, 24.067 mmol) (starting compound 1E), tert-butyl 3-formyl-1-piperidinecarboxylate (5.133 g, 24.067 mmol) (starting compound 2B), tert-butylcyanoacetate (3.398 g, 24.067 mmol), and ammonium acetate (5.432 g, 72.202 mmol) in 1,2-dimethoxyethane (24 mL) was stirred at 100° C. in a sealed tube overnight. After cooled to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was diluted with 30 mL of dichloromethane, and MnO2 was added to the mixture, and then the mixture was stirred at room temperature for 5 hrs. The mixture was filtered on Celite®, and concentrated under reduced pressure. The resulting residue (liquid) was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1) to give tert-butyl 2-amino-6-[2,6-bis(benzyloxy)phenyl]-4-[1-(tert-butoxycarbonyl)-3-piperidinyl]nicotinate as a pale yellow oil. (2.5 g, yield; 16%)

후처리

  1. temperatureAfter cooled to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was diluted with 30 mL of dichloromethane, and MnO2
  8. additionwas added to the mixture
  9. stirringthe mixture was stirred at room temperature for 5 hrs
  10. filtrationThe mixture was filtered on Celite®
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue (liquid) was purified by column chromatography on silica gel (hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-7ac53b08e2c04dff9257a7fa34506b80
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984649B1

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