Iodoethane → tert.-butyl (4S)-1-ethyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate

HRID 1702204Notes

Reaction equation

HRID 1702204 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.[CH2:24](I)[CH3:25]>[Ag]=O.CN(C)C=O>[CH2:24]([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])[CH3:25]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 110671601-benzyl 5-tert-butyl (5S)-2-oxoimidazolidine-1,5-dicarboxylate

Product 1

HCID 13053979tert.-butyl (4S)-1-ethyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylateYield 59.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

9.6 g of tert.-butyl (4S)-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate, 14.0 g of silver oxide, 46.8 g of ethyl iodide and 200 ml of dimethylformamide are treated in the same manner as described in Example 1-(2). 6.2 g of tert.-butyl (4S)-1-ethyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals.

Sources & evidence

ORD record
ord-33e0326f897d4d1d825a00def4778bbc
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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