(2S)-3-benzoylthio-2-methylpropionyl chloride → tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

HRID 1702210Notes

Reaction equation

HRID 1702210 reaction equation
[CH2:1]([N:5]1[CH2:9][C@@H:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].[C:24]([S:32][CH2:33][C@H:34]([CH3:38])[C:35](Cl)=[O:36])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:1]([N:5]1[CH2:9][C@@H:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:7]([C:35](=[O:36])[C@H:34]([CH3:38])[CH2:33][S:32][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chlorideHCID 23665647Potassium tert-butoxideHCID 86738844tert.-butyl (4S)-1-n-butyl-2-oxo-imidazolidine-4-carboxylate

Product 1

HCID 56633050tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylateYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of tert.-butyl (4S)-1-n-butyl-2-oxo-imidazolidine-4-carboxylate, 1.4 g of potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride (prepared from 2.8 g of (2S)-3-benzoylthio-2-methylpropionic acid and 10 ml of thionyl chloride) and 40 ml of tetrahydrofuran are treated in the same manner as described in Example 2-(2). Then, the oily residue obtained is purified by silica gel chromatography (Solvent, toluene-ethyl acetate (20:1)). 3.8 g of tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate are obtained as colorless syrup.

Workup

  1. customThen, the oily residue obtained
  2. customis purified by silica gel chromatography (Solvent, toluene-ethyl acetate (20:1))

Sources & evidence

ORD record
ord-5e2a721a796b4456bbd1a000ff11087f
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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