Methyl iodide → HCID 13477747, compound

HRID 1980299Notes

Reaction equation

HRID 1980299 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:14][NH:13][C:12]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:27][N:13]1[CH2:14][C@@H:15]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C:12]1=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13477741HCID 13477741, compound

Product 1

HCID 13477747HCID 13477747, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g of benzyl (4S)-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate, 29.3 g of anhydrous potassium carbonate, 50 g of methyl iodide and 200 ml of acetone is vigorously stirred at room temperature for 5 days. The mixture is concentrated under reduced pressure to remove solvent. Ethyl acetate and water are added to the residue, and the ethyl acetate layer is collected therefrom. The ethyl acetate solution is dried and concentrated under reduced pressure. The residue obtained is purified by silica gel chromatography and then triturated with ether. 18.2 g of benzyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are thereby obtained as colorless crystals. Yield: 60.7%

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. additionEthyl acetate and water are added to the residue
  4. customthe ethyl acetate layer is collected
  5. dry with materialThe ethyl acetate solution is dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by silica gel chromatography
  9. customtriturated with ether

Sources & evidence

ORD record
ord-c485c5a434f7425f938dc721af6c39b2
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

Loading…