Hydrochloric Acid → HCID 18675481, compound

HRID 343627Notes

Reaction equation

HRID 343627 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>O1CCOCC1.O>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:12][CH:13]2[C:17]([OH:19])=[O:18])(=[O:32])=[O:31])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 50583624-((Benzyloxy)carbonyl)piperazine-2-carboxylic acid

Product 1

HCID 18675481HCID 18675481, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of (+)4-benzyloxycarbonyl-2-piperazinecarboxylic acid (1.90 grams, 7.2 mmol) in dioxane-water (10 ml, ca. 1:1) is added 1N sodium hydroxide solution (15 ml, 15 mmol) followed by 4-methoxybenzenesulfonyl chloride. The solution is stirred for 1 hour, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The combined extracts are dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid) to provide (+)-1-(4-methoxybenzenesulfonyl)-4-benzyloxycarbonyl-2-piperazinecarboxylic acid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-a872abc4f25048dfad0ab0b8b8581ec3
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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