Triethylamine → (E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester

HRID 220182ノート

反応式

HRID 220182 の反応式
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1.[C:21]([O:25][C:26](=[O:39])[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:38])[CH:36]=[CH2:37])([CH3:24])([CH3:23])[CH3:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16](/[CH:37]=[CH:36]/[C:35](=[O:38])[NH:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:39])=[CH:15][CH:14]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 80271Tri-o-tolylphosphineHCID 20786195HCID 20786195、化合物HCID 592382632-(4-Bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester

生成物 1

HCID 59238287(E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester収率 50%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(4-bromo-phenyl)-3-(1-methyl-piperidin-4-yl)-propionic acid methyl ester (2.27 g, 6.67 mmol), (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (2 g, 7.2 mmol), Pd2(dba)3 (160 mg, 0.175 mmol), tri-o-tolylphosphine (160 mg, 0.526 mmol) and triethylamine (1.6 g, 15.8 mmol) in DMF (12 mL) was stirred at 100 degrees Celsius under N2 for 4 hours. After cooling to room temperature, the mixture was poured into a saturated aqueous solution of NH4Cl, and extracted with ethyl acetate (80 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and purified by flash column chromatography to obtain a pale yellow solid (1.74 g, 50%). MS: calc'd 522 (MH+), exp 522 (MH+).

後処理

  1. extractionextracted with ethyl acetate (80 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-01faed2728e946bd9ab4e6be7a148f19
出典データセット
uspto-grants-2012_06
特許番号
US08202866B2

反応ノート

読み込み中…