Sodium Hydroxide → HCID 13504321, compound

HRID 2166277Notes

Reaction equation

HRID 2166277 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9](=[O:31])[C@H:10]2[CH2:14][C@H:13]([O:15]C=O)[CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:31])[C@H:10]2[CH2:14][C@H:13]([OH:15])[CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15116365HCID 15116365, compound

Product 1

HCID 13504321HCID 13504321, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

215 mg of trans-1-p-nitrobenzyloxycarbonyl-4-formyloxy-D-proline p-methoxybenzyl ester was dissolved in 1.1 ml of tetrahydrofuran, and 0.93 ml of a 1N aqueous solution of sodium hydroxide was added to the resulting solution. After stirring for 10 minutes, the reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and distilled off to remove the solvent. The resulting residue was purified by silica gel thin layer chromatography to obtain trans-1-p-nitrobenzyloxycarbonyl-4-hydroxy-D-proline p-methoxybenzyl ester.

Workup

  1. washwashed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over sodium sulfate
  3. distillationdistilled off
  4. customto remove the solvent
  5. customThe resulting residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-50091ac22f254e1799e2622f1fd8b333
Source dataset
uspto-grants-1990_07
Patent number
US04943569

Reaction notes

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