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

HRID 1185612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185612
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]

Komponenten

6

Edukt 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)

Produkt 1

HCID 666204492-[1-(4-Bromo-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d493bc5172274c8da0f5c4ea14403c58
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669234B2

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