Hydrochloric Acid → HCID 54309376, compound

HRID 2270998Notes

Reaction equation

HRID 2270998 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:10][C@@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 27282172HCID 27282172, compound

Product 1

HCID 54309376HCID 54309376, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2R)-1-tert-butoxycarbonyl-2-ethoxycarbonylpiperazine (1.67 g) and 1N aqueous sodium hydroxide (9.53 ml) in dioxane (16 ml) was stirred for 2 hours at ambient temperature. The mixture was adjusted to pH 5 with 1N HCl on an ice bath. To the mixture was added sodium carbonate (1.35 g), and then methanesulfonyl chloride (873 mg) dropwise on an ice bath. After stirring at the same temperature for 2 hours, the resulting mixture was acidified with 4N HCl, and extracted with AcOEt. The extract was dried over sodium sulfate and concentrated in vacuo to give 1.95 g of (2R)-1-tert-butoxycarbonyl-4-methanesulfonylpiperazine-2-carboxylic acid as an amorphous powder.

Workup

  1. stirringAfter stirring at the same temperature for 2 hours
  2. extractionextracted with AcOEt
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf235065c77941568bbecfade223a303
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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