Acetic Acid → Tert-butyl 4-(2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxylate

HRID 550390Notes

Reaction equation

HRID 550390 reaction equation
[O-:1][C:2]#[N:3].[K+].C(O[C:8](=[O:24])[CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)C.C(O)(=O)C>O>[O:1]=[C:2]1[NH:3][C:8](=[O:24])[CH2:9][N:10]1[CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 15380724Tert-butyl 4-[(2-ethoxy-2-oxoethyl)amino]piperidine-1-carboxylate

Product 1

HCID 57428924Tert-butyl 4-(2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxylateYield 30.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Potassium cyanate (31 mg, 0.384 mmol) was added to a solution of tert-butyl 4-[(2-ethoxy-2-oxoethyl)amino]piperidine-1-carboxylate (100 mg, 0.384 mmol) in water (2 mL). Acetic acid was then added to adjust pH of reaction to 4-5 and the mixture was heated at 40° C. After 16 h, the reaction was cooled to ambient temperature and purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (33 mg).

Workup

  1. custompH of reaction to 4-5
  2. temperaturethe reaction was cooled to ambient temperature
  3. custompurified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fea543acaa994a27b3a9528640fa804d
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

Loading…