Benzyl chloroformate → HCID 54346849, compound

HRID 2271000Notes

Reaction equation

HRID 2271000 reaction equation
Cl.[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1)(=[O:5])=[O:4].C([O-])(O)=O.[Na+].[CH2:20]([O:27][C:28](Cl)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.O1CCOCC1.CCOCC>[CH2:20]([O:27][C:28]([N:9]1[CH2:10][CH2:11][N:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH2:7][C@@H:8]1[C:12]([OH:14])=[O:13])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 69972355HCID 69972355, compound

Product 1

HCID 54346849HCID 54346849, compoundYield 102.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2R)-4-methanesulfonylpiperazine-2-carboxylic acid hydrochloride (2.10 g) in H2O (20 ml) and dioxane (20 ml) were added NaHCO3 (2.38 g) and a solution of benzyloxycarbonyl chloride (1.76 g) in Et2O (10 ml) at room temperature. After stirring for 2 hours, Et2O and dioxane were evaporated in vacuo. The solution was acidified with 1N HCl and extracted with AcOEt (80 ml). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give 3.0 g of (2R)-1-benzyloxycarbonyl-4-methanesulfonylpiperazine-2-carboxylic acid as an amorphous powder.

Workup

  1. customat room temperature
  2. customEt2O and dioxane were evaporated in vacuo
  3. extractionextracted with AcOEt (80 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16d1cc937b98422994b5dae3817b6c50
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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