Bis(4-nitrophenyl) carbonate → HCID 67405859, compound

HRID 1174386Notes

Reaction equation

HRID 1174386 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C@@H:5]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:17](=O)(OC1C=CC([N+]([O-])=O)=CC=1)[O:18]C1C=CC([N+]([O-])=O)=CC=1>ClCCCl>[CH3:16][C@@H:13]([CH2:14][CH3:15])[C@H:5]([N:4]1[CH2:3][CH2:2][NH:1][C:17]1=[O:18])[C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

4

Reactant 2

HCID 78756Bis(4-nitrophenyl) carbonateHCID 86598803tert-butyl(2S,3S)-2-[(2-aminoethyl)amino]-3-methylpentanoate

Product 1

HCID 67405859HCID 67405859, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution containing the product from Example 3G (0.50 g, 2.08 mmol) in 1,2-dichloroethane (90.0 mL) was added bis(4nitrophenyl) carbonate (0.80 g, 2.63 mmol), and the mixture was heated to 70° C. for 12 hours. The reaction mixture was cooled and concentrated. The residue was dissolved in ethyl acetate, and washed with 10% Na2CO3 (3×), brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with a gradient starting with dichloromethane and ending ethyl acetate to give the product (0.49 g, 88% yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 10% Na2CO3 (3×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with a gradient

Sources & evidence

ORD record
ord-326e0fdcfb094d599eb8a464cc2a3f56
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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