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

HRID 1702206Notes

Reaction equation

HRID 1702206 reaction equation
[CH2:1]([N:3]1[CH2:7][C@@H:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[NH:5][C:4]1=[O:15])[CH3:2].CC(C)([O-])C.[K+].[C:22]([S:30][CH2:31][C@H:32]([CH3:36])[C:33](Cl)=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:1]([N:3]1[CH2:7][C@@H:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[N:5]([C:33](=[O:34])[C@H:32]([CH3:36])[CH2:31][S:30][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]1=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chlorideHCID 13053981tert.-butyl (4S)-1-ethyl-2-oxo-imidazolidine-4-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13054001tert.-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylateYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g of tert.-butyl (4S)-1-ethyl-2-oxo-imidazolidine-4-carboxylate, 1.6 g of potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride (prepared from 3.2 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)). 4.2 g of tert.-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals.

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-7407626dfc5a432a90ceb4ce96770389
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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