trans-Cinnamamide → HCID 66608942、化合物

HRID 1529553

反応式

HRID 1529553 の反応式
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

参加物

4

反応物 3

HCID 5273472trans-CinnamamideHCID 59143774HCID 59143774、化合物HCID 66613331HCID 66613331、化合物

生成物 1

HCID 66608942HCID 66608942、化合物収率 15%

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-feb9b4fcb67a4ad9888ea1dadc344e06
出典データセット
uspto-grants-2015_07
特許番号
US09090632B2

関連ノート

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