Hydrochloric Acid → HCID 19386785, compound

HRID 2399263Notes

Reaction equation

HRID 2399263 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]([S:12]C(OC(C)(C)C)=O)[CH2:9][CH:8]1[CH2:20][NH2:21])=[O:6])[CH:2]=[CH2:3].Cl>C(O)(=O)C.O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+6]>[NH2:21][CH2:20][CH:8]1[CH2:9][CH:10]([S:12][S:12][CH:10]2[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:8]([CH2:20][NH2:21])[CH2:9]2)[CH2:11][N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 19386789HCID 19386789, compound

Product 1

HCID 19386785HCID 19386785, compound

Reagents, catalysts & solvents 3

HCID 11963580Ferrate(4-), hexakis(cyano-C)-, tetrapotassium, (OC-6-11)-CatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1-allyloxycarbonyl-2-aminomethyl-4-t-butoxycarbonylthiopyrrolidine (10 mmol) in acetic acid (25 ml), was saturated with hydrogen chloride and heated on a steam bath for 5 minutes. The solution was filtered and the filtrate evaporated. The residue was taken up in 2.5N aqueous solution of sodium hydroxide (25 ml) and ethanol (10 ml). A solution of potassium hexacyanoferrate (11 mmols) in water (20 ml) was added portion wise until a yellow colour persisted. The reaction was stirred at room temperature for 1 hour. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with water, a saturated aqueous solution of sodium chloride and dried (MgSO4). The solvent was removed by evaporation to give diallyl 4,4'-dithiodi[2-(aminomethyl)pyrrolidin-1-carboxylate] as a brown oil. NMR (DMSO-d6): 1.88(m,1H); 2.34(m,2H); 2.87(m, partially obscured); 3.20(m,1H); 3.55(m,1H); 3.76(m, 1H); 3.90(m,1H); 4.5 (m,1H); 5.2(m,2H); 5.94(m,1H): M/S CI (M+H)+= 431.

Workup

  1. temperatureheated on a steam bath for 5 minutes
  2. filtrationThe solution was filtered
  3. customthe filtrate evaporated
  4. customThe reaction mixture was partitioned between water and dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried (MgSO4)
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ff0cd9d4c2a443748100adb391b6a1e2
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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