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

HRID 1980296Notes

Reaction equation

HRID 1980296 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.[C:24](=O)([O-])[O-].[K+].[K+].CI>CC(C)=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

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 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 89.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9.6 g of tert.-butyl (4S)-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 200 ml of acetone, and 8.3 g of anhydrous potassium carbonate and 14.2 g of methyl iodide are added thereto. The mixture is stirred at room temperature for 6 days. The reaction mixture is treated in the same manner as described in Preparation 1-(2), whereby 9.0 g of tert.-butyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals. Yield: 89.8% The physico-chemical properties of this product are identical with those of the sample obtained in Preparation 1-(2).

Workup

  1. additionThe reaction mixture is treated in the same manner
  2. customas described in Preparation 1-(2)

Sources & evidence

ORD record
ord-cc448798c0ae4d1aaeb70df8e393f9d4
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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