Hydrochloric Acid → HCID 10339094, compound

HRID 2081172Notes

Reaction equation

HRID 2081172 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@H:4]([CH2:20][SH:21])[NH:5][CH2:6][C:7]([S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:9])[CH3:8].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24].Cl>CN(C)C=O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][S:10][C:7]([CH3:9])([CH3:8])[CH2:6][N:5]2[C@H:4]([C:3]([O:2][CH3:1])=[O:22])[CH2:20][S:21][C:23]2=[O:24])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 10472632HCID 10472632, compound

Product 1

HCID 10339094HCID 10339094, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[2-(4-methoxybenzylthio)-2-methylpropyl]-L-cysteine methyl ester (0.6 g) in dimethylformamide (DMF,10 ml), carbonyldiimidazole (0.34 g) was added and the mixture was stirred for 2.5 hr at 110°-120° C. After the addition of hydrochloric acid to the reaction mixture, the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water and then saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.35 g of (4R)-3-[2-(4-methoxybenzylthio)-2-methylpropyl]-4-methoxycarbonylthiazolidine-2-one.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, water
  3. dry with materialsaturated sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-560fcf3e20014554a4f9fc80ece7b3f2
Source dataset
uspto-grants-1993_02
Patent number
US05183816

Reaction notes

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