Diisopropylethylamine → (S)-tert-Butyl 2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate

HRID 524991ノート

反応式

HRID 524991 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:49][N:50]1[CH:54]=[CH:53][CH:52]=[C:51]1[C:55]([NH:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:56]>CN(C)C=O>[C:58]1([NH:57][C:55]([C:51]2[N:50]([NH:49][C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][N:8]3[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])[CH:54]=[CH:53][CH:52]=2)=[O:56])[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

生成物 1

HCID 70922354(S)-tert-Butyl 2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S)-1-(tert-Butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.80 g, 8.36 mmol) were dissolved in 20 ml of N,N-dimethylformamide and HATU (3.40 g, 8.95 mmol), DIEA (2.60 ml, 14.89 mmol) and 1-amino-N-phenyl-1H-pyrrole-2-carboxamide were added. The resulting solution was stirred at room temperature overnight and the solvent was removed in vacuum. The residue was taken up in ethyl acetate and the organic solution was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to dryness. The crude product was purified by flash chromatography (0% to 30% hexane/AcOEt) to yield 1.90 g (62%) of the title compound as a white solid.

後処理

  1. customthe solvent was removed in vacuum
  2. washthe organic solution was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (0% to 30% hexane/AcOEt)

出典と根拠

ORDレコード
ord-cf3d02c3a6be41e89a3272e2846e4fdf
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…