Hydrochloric Acid → HCID 10339094, compound

HRID 1590162Notes

Reaction equation

HRID 1590162 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 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[2-(4-methoxybenzylthio)-2-methylpropyl]-L-cysteine methyl ester (0.5 g) in dimethylformamide (10 ml), carbonyldiimidazole (0.28 g) was added and the mixture was stirred for 2.5 hours at 100°-110° C. 1N hydrochloric acid was added into the reaction mixture and 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 magnesium sulfate, and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography and recrystallized from n-hexane--isopropanol to give 0.22 g (40%) of the titled compound.

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 magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-bc91f4f6d38e4c9e8bff4b745182739d
Source dataset
uspto-grants-1993_04
Patent number
US05202342

Reaction notes

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