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

HRID 1702214Notes

Reaction equation

HRID 1702214 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:10][C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:27]([S:35][CH2:36][C@H:37]([CH3:41])[C:38](Cl)=[O:39])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[N:10]([C:38](=[O:39])[C@H:37]([CH3:41])[CH2:36][S:35][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chlorideHCID 13053983tert-butyl (S)-1-benzyl-2-oxoimidazolidine-4-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13193172tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylateYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27.6 g of tert.-butyl (4S)-1-benzyl-2-oxo-imidazolidine-4-carboxylate, 11.2 g of potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride (prepared from 22.4 g of (2S)-3-benzoylthio-2-methylpropionic acid and 25 ml of thionyl chloride) and 200 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)) and triturated with n-hexane. 34.1 g of tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate are obtained as colorless crystals. Yield: 70.7%

Workup

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

Sources & evidence

ORD record
ord-8db01cf9033e41d0806f2632996cc33d
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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