1,1'-Thiocarbonyldiimidazole → HCID 9952107, compound

HRID 2081171Notes

Reaction equation

HRID 2081171 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)=[S:24]>C(Cl)(Cl)Cl>[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=[S:24])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 10472632HCID 10472632, compound

Product 1

HCID 9952107HCID 9952107, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-[2-(4-methoxybenzylthio)-2-methylpropyl]-L-cysteine methyl ester (5.0 g) in chloroform (90ml), thiocarbonyldiimidazole (3.0 g) was added and the mixture was stirred for 1.5 hr at room temperature. The reaction mixture was washed with 3N 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 5.10 g(91%) of (4R)-3-[2-(4-methoxy-benzylthio)-2-methylpropyl]-4-methoxycarbonylthiazolidine-2-thione.

Workup

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

Sources & evidence

ORD record
ord-380b7823292147c18d369b4b734c7992
Source dataset
uspto-grants-1993_02
Patent number
US05183816

Reaction notes

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