Sodium Hydroxide → 4-Benzyl-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

HRID 2079770Notes

Reaction equation

HRID 2079770 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4].[OH-].[Na+]>CO>[C:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][N:9]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][C@H:5]1[C:3]([OH:4])=[O:2])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58367486HCID 58367486, compound

Product 1

HCID 407870284-Benzyl-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the round bottom flask containing compound 3 (720 mg, 2.15 mmol) is added MeOH (20 ml) followed by 1 N NaOH (12.9 ml, 12.9 mmol) and stirred overnight at room temperature at which point LCMS shows product peak at 321 (M+H). The reaction mixture is concentrated under reduced pressure to remove methanol. Acidified to pH around three with acetic acid. The mixture is then extracted with DCM and the organic is washed with water twice and once with brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to get white solid 4 (615 mg, 89% yield). HPLC shows compound 4 to be greater than 98% pure.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove methanol
  3. extractionThe mixture is then extracted with DCM
  4. washthe organic is washed with water twice
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ad47fe4cb049efa12cd863eb468ecf
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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