Hydrochloric Acid → HCID 18675481, compound

HRID 1635066Notes

Reaction equation

HRID 1635066 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH:12]1C(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:20].[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.[O:35]1[CH2:40]COCC1.O>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH:15]2[C:40]([OH:35])=[O:20])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 147513461-((Benzyloxy)carbonyl)piperazine-2-carboxylic acidHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 18675481HCID 18675481, compound

Procedure

To a solution of (±)-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 (eluton 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 (eluton with 2:1 ethyl acetate-hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-89948552421b4ad989d8236ffe5519c9
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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