trans-Cinnamamide → HCID 66608942, 화합물

HRID 1529553

반응식

HRID 1529553 반응식
CC(OC([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[CH:11](Br)[CH2:10][CH2:9]1)=O)(C)C.CC(OC(N1CCCC(=O)C(Br)C1)=O)(C)C.[C:33]([NH2:43])(=O)/[CH:34]=[CH:35]/[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[C:36]1(/[CH:35]=[CH:34]/[C:33]2[O:15][C:12]3[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=3[N:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

4

반응물 3

HCID 5273472trans-CinnamamideHCID 59143774HCID 59143774, 화합물HCID 66613331Tert-butyl 3-bromo-4-oxo-azepane-1-carboxylate

생성물 1

HCID 66608942HCID 66608942, 화합물수율 15%

반응 조건

온도
120 °C

실험 절차

A mixture of 4-bromohexahydro-5-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester and 3-bromohexahydro-4-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester (0.22 g, 0.50 mmol) and trans-cinnamamide (0.06 g, 0.38 mmol) was supported in silica gel (1 g) and mechanically stirred at 120° C. for 3 days. The product was eluted from the silica gel with a 7M solution of ammonia in MeOH and the filtrate evaporated in vacuo. The crude product was basified with a saturated solution of NaHCO3 and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine (0.045 g, 15% yield, 32% pure) as a brown solid that was used in the next step without further purification. C15H16N2O LCMS: Rt 1.60, m/z 241 [M+H]+ (method 5). The compound 3-bromohexahydro-4-oxo-1H-azepine-1-carboxylic acid 1,1-dimethylethyl ester was not observed in the crude of the reaction.

후처리

  1. washThe product was eluted from the silica gel with a 7M solution of ammonia in MeOH
  2. customthe filtrate evaporated in vacuo
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-feb9b4fcb67a4ad9888ea1dadc344e06
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090632B2

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