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

HRID 216280

Reaction equation

HRID 216280 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)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]

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 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.

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. filtrationfiltered
  7. customthe solvents were evaporated
  8. customthe residue was purified

Sources & evidence

ORD record
ord-3e2bf8de5c0d4887bfae56ade6fdb079
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Linked notes

Loading…