Pyridinium, 1-(2,4-dinitrophenyl)-, chloride (1:1) → HCID 67705543, compound

HRID 975701Notes

Reaction equation

HRID 975701 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][CH2:33][NH2:34])=[O:6])[CH:2]=[CH2:3].[Cl-:35].[N+]([C:39]1[CH:44]=[C:43]([N+]([O-])=O)C=[CH:41][C:40]=1[N+]1C=CC=CC=1)([O-])=O>C(O)CCC>[Cl-:35].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][CH2:33][N+:34]1[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 77850Pyridinium, 1-(2,4-dinitrophenyl)-, chloride (1:1)HCID 22870381HCID 22870381, compound

Product 1

HCID 67705543HCID 67705543, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (2R,4S)-1-allyloxycarbonyl-2-(2aminoethyl)4-(triphenylmethylthio) pyrrolidine (5.78 g) and 1-(2,4-dinitrophenyl)pyridinium chloride (4.19 g) in n-butanol (60 ml) was stirred under reflux condition for 4 hours, and then evaporated under reduced pressure. The residue was column chromatographed on silica gel (chloroform:methanol=5:1 to 4:1) to give (2R,4S)-1-allyloxycarbonyl-2-{2-(1-pyridinio)ethyl}-4(triphenylmethylthio)pyrrolidine chloride (5.88 g).

Workup

  1. temperatureunder reflux condition for 4 hours
  2. customevaporated under reduced pressure
  3. customchromatographed on silica gel (chloroform:methanol=5:1 to 4:1)

Sources & evidence

ORD record
ord-e1af59c779a64982b2659e6111423373
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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