1,1'-Thiocarbonyldiimidazole → HCID 9952107, compound

HRID 1656900Notes

Reaction equation

HRID 1656900 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-thion

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-5fa16ca42c0f46718bbe8d3212e1a229
Source dataset
uspto-grants-1993_10
Patent number
US05256655

Reaction notes

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