Potassium Carbonate → HCID 59124109, compound

HRID 1268759Notes

Reaction equation

HRID 1268759 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C@@:7]2([C:13]([O:15]C)=O)[CH2:11][C@@H:10]([OH:12])[CH2:9][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:25][C:26]1[CH:27]=[C:28]([N:33]=[C:34]=[O:35])[CH:29]=[C:30]([Cl:32])[CH:31]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]23[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]2[C:34](=[O:35])[N:33]([C:28]2[CH:29]=[C:30]([Cl:32])[CH:31]=[C:26]([Cl:25])[CH:27]=2)[C:13]3=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanateHCID 58840800HCID 58840800, compound

Product 1

HCID 59124109HCID 59124109, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl (4R)-2-(4-bromobenzyl)-4-hydroxy-L-prolinate (0.170 g) (Prep. 3) in 10 mL of DMF was added K2CO3 (0.15 g). The reaction mixture was cooled to 0° C., treated with 3,5-dichlorophenyl isocyanate (0.116 g), then allowed to warm to RT and stirred overnight. The insoluble material was removed by filtration, the DMF evaporated, and the residue dissolved in DCM. The organic layer was washed with water, dried over MgSO4, and evaporated under reduced pressure. The resulting oily residue was purified over SiO2 isolute column (10 g) (eluent: DCM/acetone-95/5) to afford the above-titled compound (0.100 g) as a white solid. 1H NMR (CDCl3): 7.45 (2H,d), 7.30 (1H,m), 7.10 (2H,d), 6.85 (2H,d), 4.75 (1H,m), 4.10 (1H,dd), 3.45 (1H,d), 3.40 (1H,dd), 3.25 (1H,d), 2.35 (1H, dd), 2.20 (1H,dd).

Workup

  1. temperatureto warm to RT
  2. customThe insoluble material was removed by filtration
  3. customthe DMF evaporated
  4. dissolutionthe residue dissolved in DCM
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe resulting oily residue was purified over SiO2 isolute column (10 g) (eluent: DCM/acetone-95/5)

Sources & evidence

ORD record
ord-0e0eeda510ef4558868e52212c1fd3f7
Source dataset
uspto-grants-2007_04
Patent number
US07199125B2

Reaction notes

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