Sodium Hydroxide → 2-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acid

HRID 2243847Notes

Reaction equation

HRID 2243847 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22321826tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylate

Product 1

HCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-ethoxycarbonylmethyl-piperazine-1-carboxylic acid tert-butyl ester (1.3 g, 4.78 mmol) in methanol (50 ml) was treated with NaOH (1N, 10 ml, 10 mmol) and stirred for 4 h. The mixture is concentrated and the residue is adjusted to pH 6 with 5% citric acid solution. The mixture is extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 4-carboxymethyl-piperazine-1-carboxylic acid tert-butyl ester, 445 mg (38%) as a white solid. ESI MS m/z 1179 (M+H+); 1H NMR (400 MHz, CDCl3) δ 3.80-3.60 (m, 4H), 3.42 (s, 2H), 3.10-2.84 (m, 4H), 1.24 (s, 9H).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-776ae325d9ed43b1bd1f4313eba5ca81
Source dataset
uspto-grants-2010_03
Patent number
US07678791B2

Reaction notes

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