Diisopropylethylamine → HCID 56851159、化合物

HRID 1690776ノート

反応式

HRID 1690776 の反応式
[F:1][C:2]([F:16])([F:15])[C@H:3]([CH3:14])[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[O:48]1[CH2:53][CH2:52][CH:51]([C:54]2[CH:55]=[C:56]3[C:60](=[CH:61][CH:62]=2)[CH2:59][NH:58][CH2:57]3)[CH2:50][CH2:49]1>CN(C=O)C>[O:48]1[CH2:53][CH2:52][CH:51]([C:54]2[CH:55]=[C:56]3[C:60](=[CH:61][CH:62]=2)[CH2:59][N:58]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C@@H:3]([CH3:14])[C:2]([F:1])([F:16])[F:15])=[O:9])[CH2:57]3)[CH2:50][CH2:49]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 56851158HCID 56851158、化合物HCID 577536035-(tetrahydro-pyran-4-yl)-2,3-dihydro-1H-isoindole

生成物 1

HCID 56851159HCID 56851159、化合物収率 94.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 0.9 g (3.8 mmol) 2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid in 9 ml DMF under argon at room temperature, was added 1.4 g (4.2 mmol) TBTU, 3.3 ml (19.2 mmol) N-ethyldiisopropylamine and finally 0.8 g (3.8 mmol) 5-(tetrahydro-pyran-4-yl)-2,3-dihydro-1H-isoindole (CAS: 905274-50-2). The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed twice with water and twice with sat. NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 1.5 g (93%) of the title compound as a yellow oil. MS (m/e): 420.2 [M+H]+.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed twice with water and twice with sat. NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  8. customformed from heptane and ethylacetate

出典と根拠

ORDレコード
ord-7acfb2c2330b4cd1b1c27073f97d6a2e
出典データセット
uspto-grants-2012_04
特許番号
US08153679B2

反応ノート

読み込み中…