Acetic Acid → HCID 14830195, compound

HRID 1088256Notes

Reaction equation

HRID 1088256 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17]C(=O)C3C=CC=CC=3)[CH2:14][C@H:13]2CC#N)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:31]([OH:34])(=[O:33])[CH3:32]>Cl>[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[CH2:32][C:31]([OH:34])=[O:33])=[O:11])=[CH:29][CH:30]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 14830192HCID 14830192, compound

Product 1

HCID 14830195HCID 14830195, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(2R,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-cyanomethyl-4-benzoyloxypyrrolidine (3.0 g) was dissolved in 10 ml of acetic acid and 10 ml of conc. hydrochloric acid. After refluxing for 3 hours, the reaction mixture was cooled down to room temperature and distilled to remove the solvent. The residue was diluted with 4 ml of water and 25 ml of 1N sodium hydroxide solution. A solution of 1.53 g of p-nitrobenzyl chloroformate in 6 ml of diethyl ether and 2 ml of tetrahydrofuran was added to the above mixture at 0° C., followed by stirring at the same temperature for 30 minutes. The reaction mixture was separated. The aqueous layer was acidified with 6N hydrochloric acid to pH 1.0 and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to give (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-carboxymethyl-4-hydroxypyrrolidine.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. additionThe residue was diluted with 4 ml of water and 25 ml of 1N sodium hydroxide solution
  5. additionA solution of 1.53 g of p-nitrobenzyl chloroformate in 6 ml of diethyl ether and 2 ml of tetrahydrofuran was added to the above mixture at 0° C.
  6. customThe reaction mixture was separated
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-e99746d3b43a4f4990d4fb78b6410433
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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