Thionyl Chloride → tert.-butyl (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

HRID 1702202Notes

Reaction equation

HRID 1702202 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[NH:4][C:3]1=[O:14].[H-].[Na+].[C:17]([S:20][CH2:21][C@H:22]([CH3:26])[C:23](Cl)=[O:24])(=[O:19])[CH3:18].C(SC[C@@H](C)C(O)=O)(=O)C.S(Cl)(Cl)=O>O1CCCC1>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[N:4]([C:23](=[O:24])[C@H:22]([CH3:26])[CH2:21][S:20][C:17](=[O:19])[CH3:18])[C:3]1=[O:14]

Participants

7

Reactant 5

HCID 24386Thionyl Chloride2×HCID 24758Sodium hydrideHCID 2724506D-beta-acetylthioisobutyric acidHCID 10954137S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioateHCID 13053976tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate

Product 1

HCID 13053996tert.-butyl (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylateYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.3 g of tert.-butyl (4S)-1-methyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 15 ml of tetrahydro-furan, and 0.35 g of sodium hydride (62% oil dispersion) is added thereto under ice-cooling and stirring. A solution of (2S)-3-acetylthio-2-methylpropionyl chloride (prepared by heating a mixture of 1.5 g of (2S)-3-acetylthio-2-methylpropionic acid and 6 ml of thionyl chloride at 50° C. for 3 hours and then evaporting excess thionyl chloride under reduced pressure) in 5 ml of tetrahydrofuran is added dropwise to the mixture. Then, the mixture is treated in the same manner as described in Example 1-(4). 1.0 g of tert.-butyl (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxoimidazolidine-4-carboxylate is obtained as colorless crystals.

Workup

  1. temperatureunder ice-cooling
  2. temperatureby heating
  3. additionThen, the mixture is treated in the same manner

Sources & evidence

ORD record
ord-e961a187165b4a15ad87142b4c50ee92
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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