Potassium Carbonate → HCID 71230561, compound

HRID 1746275Notes

Reaction equation

HRID 1746275 reaction equation
[O:1]=[C:2]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:3][NH:4][C:5](OCC)=[O:6].C([O-])([O-])=O.[K+].[K+]>C(O)C>[O:6]=[C:5]1[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:2](=[O:1])[NH:3][NH:4]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 71230584HCID 71230584, compound

Product 1

HCID 71230561HCID 71230561, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To ethyl 4,11-dioxo-13-phenyl-12-oxa-2,3,5,10-tetraazatridecan-1-oate (I-9a: 965 mg, 2.74 mmol) in ethanol (11.000 mL) was added K2CO3 (1514 mg, 10.95 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 a pH of approximately 4. The resultant white solid was filtered, rinsed with some methanol, and then concentrated in vacuo. The residue was purified by silica gel chromatography (40-100% ethyl acetate/heptane) giving benzyl 4-(3,5-dioxo-1,2,4-triazolidin-4-yl)butylcarbamate (I-9b: 369 mg, 44%) as a white solid. LC-MS (M+1) 307.1, t=0.78 minute. 1H NMR (400 MHz, MeOD) δ ppm 1.40-1.58 (m, 2 H) 1.58-1.74 (m, 2 H) 3.15 (t, J=6.82 Hz, 2 H) 3.51 (t, J=6.95 Hz, 2 H) 5.06 (s, 2 H) 7.21-7.42 (m, 5 H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. addition4N HCl in dioxane was added up to a pH of approximately 4
  4. filtrationThe resultant white solid was filtered
  5. washrinsed with some methanol
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (40-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-4e241daa5b974ca5a81330b12201a07f
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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