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

HRID 643077Notes

Reaction equation

HRID 643077 reaction equation
[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=O)C>[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product of Example 28D in DMF (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 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.

Workup

  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. customthe solvents were evaporated
  7. customthe residue was purified

Sources & evidence

ORD record
ord-525fe61204e2427095513d5b02240dd2
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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