Diisopropylethylamine → HCID 86722063、化合物

HRID 525046ノート

反応式

HRID 525046 の反応式
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([NH:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[O:9].[CH2:19]([O:26][C@H:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:29]([C:39](O)=[O:40])[CH2:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C)C=O.O>[CH2:19]([O:26][C@H:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[C@H:29]([C:39](=[O:40])[NH:1][N:2]2[CH:6]=[CH:5][C:4]([Br:7])=[C:3]2[C:8](=[O:9])[NH:10][C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)[CH2:28]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 11860409Boc-Hyp(Bzl)-OHHCID 70978853HCID 70978853、化合物

生成物 1

HCID 86722063HCID 86722063、化合物収率 74.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

1-Amino-3-bromo-N-(3,5-difluorophenyl)-1H-pyrrole-2-carboxamide (1.5 g, 4.75 mmol), (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (0.99 g, 3.08 mmol) and diisopropylethylamine (2.8 ml, 16.08 mmol) were dissolved in dimethylformamide (30 ml) and the mixture cooled at 0° C. To this mixture, T3P (50% solution in ethyl acetate, 2.1 ml, 7.19 mmol) dissolved in DMF (5 ml) was dropwise added. Once the addition is over, the mixture was stirred at room temperature for 48 h. To this mixture, water was added and extracted twice with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate, filtered and the solvents evaporated under reduced pressure. The residue was purified by flash chromatography (0% to 25% hexanes/AcOEt) to yield 1.42 g (74% yield) of the title compound.

後処理

  1. additionwas dropwise added
  2. additionOnce the addition
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvents evaporated under reduced pressure
  8. customThe residue was purified by flash chromatography (0% to 25% hexanes/AcOEt)

出典と根拠

ORDレコード
ord-76a02780c1864bdb86a2f29529021f95
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

反応ノート

読み込み中…