Pyridine → HCID 10650105, compound

HRID 1034476Notes

Reaction equation

HRID 1034476 reaction equation
[CH3:1][O:2][C:3]1[CH:55]=[CH:54][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13][C@H:12]2[CH2:36][NH:37][S:38](=[O:53])(=[O:52])[NH:39][C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)=[O:41])=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1>ClCCl.CO.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([SH:16])[CH2:13][C@H:12]2[CH2:36][NH:37][S:38](=[O:52])(=[O:53])[NH:39][C:40]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=2)=[O:41])=[O:10])=[CH:54][CH:55]=1

Participants

7

Reactant 2

HCID 1049PyridineHCID 10605273HCID 10605273, compound

Product 1

HCID 10650105HCID 10650105, compoundYield 92.4%

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-p-methoxybenzyloxycarbonylsulfamoylaminomethyl-4-tritylthiopyrrolidine (2.35 g: 3.13 mmole) in a mixture of dichloromethane (60 ml) and methanol (30 ml), a solution of pyridine (0.38 ml: 4.75 mmole: 1.5 eq.) and silver nitrate (0.80 g: 1.5 eq.) in water (2 ml) is added under ice cooling. The mixture is stirred for 10 minutes. The reaction mixture is poured into water and extracted with dichloromethane. The extract is dried over magnesium sulfate and filtered. Hydrogen sulfide is passed through the filtrate and the resulting precipitate is filtered off. The filtrate is concentrated in vacuo and the residue is purified by silica gel column chromatography to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-p-methoxybenzyloxycarbonylsulfamoylaminomethyl-4-mercaptopyrrolidine (1.56 g). Yield: 92.4%. NMR δ(CDCl3) ppm: 2.42 to 2.58(m, 1H), 3.80(s, 6H), 5.08, 5.02(ABq, J=12 Hz, 2H), 5.12, 5.07(ABq, J=16 Hz, 2H). IR ν (CHCl3)cm-1 : 3380, 1740, 1685, 1610.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract is dried over magnesium sulfate
  3. filtrationfiltered
  4. filtrationthe resulting precipitate is filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ea31c9a57874b41babea2ae0f881dac
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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