Triphenylphosphine → tert-butyl(2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2,4-dioxo-1-imidazolidinyl}butanoate

HRID 1174192Notes

Reaction equation

HRID 1174192 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH2:4][N:3]1[C@@H:8]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:20][C:21]1[N:26]=[C:25]([CH2:27]O)[CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.O>[CH3:17][C:16]([CH3:19])([CH3:18])[C@H:8]([N:3]1[CH2:4][C:5](=[O:7])[N:6]([CH2:27][C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:20])[N:26]=2)[C:2]1=[O:1])[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 707366-Methyl-2-pyridylmethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67406589tert-butyl(2S)-2-(2,4-dioxo-1-imidazolidinyl)-3,3-dimethylbutanoate

Product 1

HCID 67406512tert-butyl(2S)-3,3-dimethyl-2-{3-[(6-methyl-2-pyridinyl)methyl]-2,4-dioxo-1-imidazolidinyl}butanoateYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 46C (0.112 g, 0.413 mmol) in dichloromethane (3 mL) at 0° C. was treated with 6-methyl-2-pyridinemethanol (0.056 g, 0.454 mmol), triphenylphosphine (0.141 g, 0.537 mmol), followed by diethyl azodicarboxylate (0.084 mL, 0.537 mmol), stirred at 25° C. for 16 hours, treated with water (3 mL), stirred for 2 hours at 25° C., and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane to give the title compound (0.151 g, 97% yield).

Workup

  1. stirringstirred for 2 hours at 25° C.
  2. custompartitioned between dichloromethane and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-b8be28470e1a43069abb4932ab3eda6e
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…