Bis(4-nitrophenyl) carbonate → tert-butyl(2S,3S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}pentanoate

HRID 216280

Reaktionsgleichung

Reaktionsgleichung von HRID 216280
[CH3:1][C@@H:2]([CH2:23][CH3:24])[C@H:3]([NH:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[N+](C1C=C[C:31]([O:34]C(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O>CN(C)C=O>[CH3:1][C@@H:2]([CH2:23][CH3:24])[C@H:3]([N:11]1[CH2:12][CH2:13][N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[C:31]1=[O:34])[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5]

Komponenten

4

Edukt 2

HCID 78756Bis(4-nitrophenyl) carbonateHCID 86598719tert-butyl(2S,3S)-3-methyl-2-[(2-{[(6-methyl-2-pyridinyl)methyl]amino}ethyl)amino]pentanoate

Produkt 1

HCID 86598718tert-butyl(2S,3S)-3-methyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2-oxo-1-imidazolidinyl}pentanoateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the product of Example 32D in N,N-dimethylformamide (60 mL) was treated with bis-(p-nitrophenyl)carbonate (12.6 g, 1.2 equivalents) at 50° C. for 5 hrs. The solvents were evaporated, and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4, filtered, and the solvents were evaporated, and the residue was purified using ethyl acetate:hexanes (2:1) to give 7.3 g (57%) of the title compound.

Aufarbeitung

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were evaporated
  8. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-3e2bf8de5c0d4887bfae56ade6fdb079
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193227B2

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