Diisopropylethylamine → 2-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 71685

反応式

HRID 71685 の反応式
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19](C(O)=O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN([C:28]([O:32]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:49]([O:51][C:52](=[O:63])[C:53]([NH2:62])([C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1)[CH3:54])[CH3:50]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH2:20][CH:21]1[C:28](=[O:32])[NH:62][C:53]([C:55]1[CH:56]=[CH:57][C:58]([Br:61])=[CH:59][CH:60]=1)([C:52]([O:51][CH2:49][CH3:50])=[O:63])[CH3:54])=[O:16])([CH3:11])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acidHCID 3494252Ethyl 2-amino-2-(4-bromophenyl)propanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 666204492-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester収率 58.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N,N-diisopropylethylamine (4.1 mL, 23.6 mmol) was added dropwise to a mixture of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.7 g, 3.2 mmol), HATU (1.2 g, 3.2 mmol) and 2-amino-2-(4-bromo-phenyl)-propionic acid ethyl ester (0.8 g, 2.9 mmol) in DMF (20 mL), and stirred at ambient condition for 3 hours. Most of the volatile component was removed in vacuo, and the resulting residue was dissolved in ethyl acetate (150 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a colorless oil (0.8 g, 58%). m/z 490.9, 492.9 (M+Na)+.

後処理

  1. customMost of the volatile component was removed in vacuo
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d26cd7743c354e00a867d948ff49cd64
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

関連ノート

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