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Nitromethane → HCID 86722944, 화합물

HRID 1486148
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HRID 1486148 반응식
C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C.[N+:24]([CH3:27])([O-:26])=[O:25].[CH2:28]([O:30][C:31](=[O:48])[CH:32]=[C:33]1[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:34]1)[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](=[O:48])[CH2:32][C:33]1([CH2:27][N+:24]([O-:26])=[O:25])[CH2:38][CH2:37][CH:36]([CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:34]1)[CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 86722941HCID 86722941, 화합물

생성물 1

HCID 86722944HCID 86722944, 화합물수율 96.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A sealable reaction tube was charged with 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.16 mL, 0.450 mmol) and THF (1.0 mL) under Argon. Nitromethane (0.23 mL, 4.24 mmol) was added and the reaction stirred at room temperature for 5 min then cooled to 0° C. for 15 min. [4-(tert-Butoxycarbonylamino-methyl)-cyclohexylidene]-acetic acid ethyl ester (0.261 g, 0.878 mmol) in THF (1.5 mL) was added slowly and the reaction stirred at RT for 15 min. The tube was sealed and the reaction heated at 70° C. for 17 hr. The reaction was cooled to room temperature, quenched with 0.5M HCl, and extracted with EtOAc (2×). The combined organic layers were washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated to provide 0.304 g of crude product which was carried to the next step without purification. ESI-MS m/z 359 (MH)+.

후처리

  1. additionwas added slowly
  2. stirringthe reaction stirred at RT for 15 min
  3. customThe tube was sealed
  4. temperaturethe reaction heated at 70° C. for 17 hr
  5. temperatureThe reaction was cooled to room temperature
  6. customquenched with 0.5M HCl
  7. extractionextracted with EtOAc (2×)
  8. washThe combined organic layers were washed with saturated NaHCO3 and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ae8fbf8424184da8b4744cac269179c7
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09422314B2

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