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

HRID 1064116Notes

Reaction equation

HRID 1064116 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]C)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>O1CCCC1>[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 14797Potassium HydroxideHCID 46785870Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate

Product 1

HCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acidYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 27(a) (3.6 g, 13.2 mmol) and a 5% aqueous KOH solution (90 mL, 80.0 mmol) were stirred in tetrahydrofuran (30 mL, 0.44 M) at 22° C. for 2 hours. The volatiles were removed in vacuo and treatment with strongly acidic Dowex-50™ (WX8-200), elution with ammonium hydroxide (1.0 N), and treatment with Amberlite™ CG-50 afforded Intermediate 27(b) (1.2 g) in 37% yield.

Workup

  1. customThe volatiles were removed in vacuo and treatment with strongly acidic Dowex-50™ (WX8-200), elution with ammonium hydroxide (1.0 N), and treatment with Amberlite™ CG-50 afforded Intermediate 27(b) (1.2 g) in 37% yield

Sources & evidence

ORD record
ord-8575f67de6f54ac9a8625b4c46d6ffad
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

Loading…