Methanol → HCID 56619902, compound

HRID 1088285Notes

Reaction equation

HRID 1088285 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@@H:13]2[CH2:18][C:19]([OH:21])=[O:20])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:31]O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[CH2:18][C:19]([O:21][CH3:31])=[O:20])=[O:11])=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14830193HCID 14830193, compound

Product 1

HCID 56619902HCID 56619902, compound

Procedure

(2R,4R)-1-p-Nitrobenzyloxycarbonyl-2-carboxymethyl-4-hydroxypyrrolidine (5.39 g) was dissolved in 54 ml of dry methanol, and 0.9 ml of conc. sulfuric acid was added thereto, followed by refluxing for 4 hours. The reaction mixture was neutralized with 1N sodium hydroxide solution and distilled to remove the solvent. To the residue was added ethyl acetate, and the mixture was washed with water, dried over anhydrous sodium sulfate and distilled to obtain (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-methoxycarbonylmethyl-4-hydroxypyrrolidine.

Workup

  1. temperatureby refluxing for 4 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. additionTo the residue was added ethyl acetate
  5. washthe mixture was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-30a1de7e4efb438da108e3ccaacfba61
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

Loading…