Methyl iodide → (4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester

HRID 1980294Notes

Reaction equation

HRID 1980294 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][NH:13][C:12]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]I>CN(C)C=O.C(OCC)(=O)C.[Ag]=O>[CH3:24][N:13]1[CH2:14][C@@H:15]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[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:23]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 110671601-benzyl 5-tert-butyl (5S)-2-oxoimidazolidine-1,5-dicarboxylate

Product 1

HCID 13053974(4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl esterYield 84.3%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

9.6 g of tert.-butyl (4S)-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 200 ml of dimethylformamide, and 14.0 g of silver oxide are added thereto. 42.6 g of methyl iodide are added to the mixture at room temperature under stirring, and the mixture is further stirred for 2 days in the dark. The reaction mixture is filtered to remove insoluble materials, and the filtrate is concentrated under reduced pressure. The residue obtained is dissolved in ethyl acetate. Then, the ethyl acetate solution is washed with water, dried and concentrated under reduced pressure. The residue thus obtained is washed with n-hexane. 8.45 g of tert.-butyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are thereby obtained as colorless crystals. Yield: 84.3%

Workup

  1. stirringthe mixture is further stirred for 2 days in the dark
  2. filtrationThe reaction mixture is filtered
  3. customto remove insoluble materials
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue obtained
  6. washThen, the ethyl acetate solution is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. washis washed with n-hexane

Sources & evidence

ORD record
ord-75d9220cb3a94842a5a28097d4458f86
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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