Potassium Carbonate → HCID 71230594, compound

HRID 1746272Notes

Reaction equation

HRID 1746272 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[O:3][C:4](=[O:20])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:19])[NH:12][NH:13][C:14](OCC)=[O:15].C([O-])([O-])=O.[K+].[K+]>CCO>[O:19]=[C:11]1[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4](=[O:20])[O:3][C:2]([CH3:1])([CH3:22])[CH3:21])[C:14](=[O:15])[NH:13][NH:12]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86718992HCID 86718992, compound

Product 1

HCID 71230594HCID 71230594, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To ethyl 13,13-dimethyl-4,11-dioxo-12-oxa-2,3,5,10-tetraazatetradecan-1-oate (I-8a: 1.045 g, 3.28 mmol) in EtOH (13.13 mL) was added K2CO3 (1.815 g, 13.13 mmol). The mixture was stirred at 65° C. for 16 hours. Cooled to room temperature, filtered, and then 4N HCl in dioxane was added up to pH or approximately 4. The white solid was filtered, rinsed with some methanol, and then the filtrate was concentrated in vacuo. The residue was purified by silica flash chromatography (0-10% MeOH/CH2Cl2) giving tert-butyl 4-(3,5-dioxo-1,2,4-triazolidin-4-yl)butylcarbamate (388 mg, 43%) as a oily white solid. LC-MS (M−1) 271.1, t=0.73 minute. 1H NMR (400 MHz, CD3CN) δ ppm 1.39 (s, 9 H) 1.42-1.49 (m, 2 H) 1.52-1.65 (m, 2 H) 3.03 (q, J=6.40 Hz, 2 H) 3.42 (t, J=6.95 Hz, 2 H).

Workup

  1. temperatureCooled to room temperature
  2. filtrationfiltered
  3. addition4N HCl in dioxane was added up
  4. filtrationThe white solid was filtered
  5. washrinsed with some methanol
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by silica flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cec43e2a1cf443a8be9d327067c3fb15
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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