1,1'-Thiocarbonyldiimidazole → HCID 86636692, compound

HRID 409365Notes

Reaction equation

HRID 409365 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]([CH2:10][CH3:11])[C:7]([OH:9])=[O:8])=[O:4].CCN(C(C)C)C(C)C.[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22]>C1COCC1>[O:4]=[C:3]1[N:5]([CH:6]([CH2:10][CH3:11])[C:7]([OH:9])=[O:8])[C:21](=[S:22])[NH:1][CH2:2]1

Participants

5

Reactant 3

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 868782-Glycylaminobutyric acid

Product 1

HCID 86636692HCID 86636692, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(2-aminoacetamido)butanoic acid (0.5 g, 3.12 mmol) and DIPEA (1.812 g, 14.05 mmol) in anhydrous THF 10 mL is added 1,1′-thiocarbonyldiimidazole (0.834 g, 4.68 mmol) and heated to reflux overnight. The resulting reaction mixture is concentrated to dry and the pure product 2-(5-oxo-2-thioxoimidazolidin-1-yl)butanoic acid (0.24 g, 1.187 mmol, yellow solid) is obtained by column chromatography using acetic acid/DCM, 0-5% ration solvent system. 1H-NMR (CD3OD/300 MHz): 5.21 (dd, J=10.5, 5.1 Hz, 1H), 4.09 (d, J=5.4 Hz, 2H), 2.25 (m, 2H), 0.90 (t, J=7.2 Hz, 3H). MS (ES+, m/z): 200.9 (M−, 100.0).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe resulting reaction mixture
  4. concentrationis concentrated
  5. customto dry

Sources & evidence

ORD record
ord-1a6267a6a491466bb578ff58ef70676c
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

Loading…