Sodium Hydroxide → 2-CARBOXYMETHYL-3-OXO-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

HRID 2102299Notes

Reaction equation

HRID 2102299 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH:11]1[CH2:17][C:18]([O:20]CC)=[O:19])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH:11]1[CH2:17][C:18]([OH:20])=[O:19])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49354972-Ethoxycarbonylmethyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 27560512-CARBOXYMETHYL-3-OXO-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTERYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N Sodium hydroxide (11.4 mL, 11.4 mmol) was added to 2-ethoxycarbonylmethyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (2.5 g, 8.73 mmol) in methanol (20 mL) at room temperature and then stirred for 2.5 hours. The reaction mixture was concentrated, acidified with 2N HCl to pH˜2 and extracted with dichloromethane (3 times). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the titled compound (1.87 g, 83%, white foam solid). 1H NMR (CDCl3) δ (ppm): 7.68 (bs, 1H), 4.78 (m, 1H), 4.19 (m, 1H), 3.45 (m, 1H), 3.34 (m, 2H), 2.97 (m, 2H), 1.49 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane (3 times)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f118ed5f4abd41fa8385a9f535a1b25d
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

Loading…