Procysteine → HCID 131720962, compound

HRID 1456346Notes

Reaction equation

HRID 1456346 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.[ClH:10].Cl.[O:12]([CH2:16][CH:17]1[CH2:22][NH:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]1)[N+:13]([O-:15])=[O:14].P(C#N)(OCC)(OCC)=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O1CCCC1.CN(C)C1C=CN=CC=1.C(N(CC)CC)C.CN(C)C=O>[ClH:10].[O:12]([CH2:16][CH:17]1[CH2:22][NH:21][CH:20]([CH2:23][NH:24][C:7]([C@@H:5]2[CH2:4][S:3][C:2](=[O:1])[NH:6]2)=[O:9])[CH2:19][CH2:18]1)[N+:13]([O-:15])=[O:14]

Participants

9

Reactant 4

HCID 72390ProcysteineHCID 76257Diethyl cyanophosphonateHCID 90495Di-tert-butyl dicarbonate2×HCID 22106840HCID 22106840, compound

Product 1

HCID 131720962HCID 131720962, compoundYield 8.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

In 40 ml of dry tetrahydrofuran and 20 ml of dry dimethylformamide were suspended 224 mg of (4R)-2-oxo-4-thiazolidinecarboxylic acid and 350 mg of 5-nitroxymethyl-2-piperidylmethylamine dihydrochloride, and 0.94 ml of triethylamine and 0.188 ml of diethyl cyanophosphate were added thereto with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 5 hours. To the reaction mixture were added 0.463 ml of di-t-butyl dicarbonate and a catalytic amount of 4-dimethylaminopyridine, and the resulting mixture was stirred at room temperature for 1 hour. Further, 2.0 ml of di-t-butyl dicarbonate was added thereto and the mixture was stirred at 30° C. for 1.5 hours. The insolubles were filtered and the solvent was distilled off under reduced pressure. The residue was purified by using silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=2/3-1/6) and the fraction having an Rf of 0.14 by thin layer chromatography (developing solvent: cyclohexane/ethyl acetate=1/2) was collected by separation. The thus obtained foam was dissolved in 5.0 ml of 4N hydrochloric acid-dioxane and the mixture was stirred at room temperature for 30 minutes. To the mixture was added 20 ml of ether, and the crystal was collected by filtration to obtain 40 mg of the desired compound as a pale yellow crystalline solid.

Workup

  1. additionwere added
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred at room temperature for 5 hours
  4. stirringthe mixture was stirred at 30° C. for 1.5 hours
  5. filtrationThe insolubles were filtered
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified
  8. washsilica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=2/3-1/6)
  9. customwas collected by separation
  10. dissolutionThe thus obtained foam was dissolved in 5.0 ml of 4N hydrochloric acid-dioxane
  11. stirringthe mixture was stirred at room temperature for 30 minutes
  12. additionTo the mixture was added 20 ml of ether
  13. filtrationthe crystal was collected by filtration

Sources & evidence

ORD record
ord-1199aee33ff240c5b664330fa5cebe47
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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