Ammonium dithiocarbamate → HCID 178459667, compound

HRID 1374436Notes

Reaction equation

HRID 1374436 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C:14]([C:15](=O)[CH2:16]Cl)=[CH:13][CH2:12][N:11]1[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25](=[S:28])([S-:27])[NH2:26].[NH4+]>CO.C(N)(=S)C1C=CN=CC=1>[Si:1]([O:8][CH2:9][C@@H:10]1[C:14]([C:15]2[N:26]=[C:25]([SH:28])[S:27][CH:16]=2)=[CH:13][CH2:12][N:11]1[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11083854Ammonium dithiocarbamateHCID 86592532HCID 86592532, compound

Product 1

HCID 178459667HCID 178459667, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 27237884-PyridinecarbothioamideCatalystHCID 887MethanolSolvent

Procedure

To a solution of allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(chloroacetyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (163 mg, 0.44 mmol) in methanol (2 ml) were added at 0–5° C. thioisonicotinamide (2 mg) and ammonium dithiocarbamate (72 mg, 0.65 mmol). The reaction mixture was raised to room temperature and stirred for 40 minutes. The mixture was stirred at 65–70° C. for 30 minutes and then at 75–85° C. for 1 hour. The solvent was removed in vacuo. To the solution was added ethyl acetate and the solution was separated with a separating funnel. The aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was recrystallized from ethyl acetate/hexane to give allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(2-mercapto-1,3-thiazol-4-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (70.5 mg, 39%).

Workup

  1. stirringThe mixture was stirred at 65–70° C. for 30 minutes
  2. waitat 75–85° C. for 1 hour
  3. customThe solvent was removed in vacuo
  4. additionTo the solution was added ethyl acetate
  5. customthe solution was separated with a separating funnel
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe organic layer was washed twice with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed in vacuo
  10. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-84c56d7ce47c4ff49f3ddeeb31c490ba
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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