1,1'-Carbonyldiimidazole → HCID 86690097, compound

HRID 520381Notes

Reaction equation

HRID 520381 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[O:19]=[C:18]1[N:4]([C:5]2([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]2)[CH2:3][CH2:2][O:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21623616HCID 21623616, compound

Product 1

HCID 86690097HCID 86690097, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1-((2-hydroxyethyl)amino)cyclopropanecarboxylate (0.180 g, 1.039 mmol) and CDI (0.177 g, 1.091 mmol) in THF (5 mL) was stirred at room temperature for 15 h, then heated to reflux for 15 h. The solvent was removed and the residue was purified with silica gel chromatography to yield ethyl 1-(2-oxooxazolidin-3-yl)cyclopropanecarboxylate (0.2 g). A solution of LiOH (0.048 g) in water (3 mL) was added to a solution of ethyl 1-(2-oxooxazolidin-3-yl)cyclopropanecarboxylate (0.2 g, 1.004 mmol) in THF (5 mL) and the resulting mixture was stirred vigorously at rt for 16 h. The reaction mixture was then diluted with water and washed with EtOAc. The aqueous layer was then acidified with 1N HCl and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to yield Cap L-5 (60 mg). 1H NMR (500 MHz, DMSO-d6) ppm 12.83 (br. s., 1H), 4.30-4.20 (m, 2H), 3.65-3.56 (m, 2H), 1.41-1.33 (m, 2H), 1.25-1.19 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 h
  3. customThe solvent was removed
  4. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-5ae790faceea4b0b8bf7f0caa9ba8f4c
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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