Water → HCID 178524256, compound

HRID 2103940Notes

Reaction equation

HRID 2103940 reaction equation
[O:1]1CC(=O)N=N1.C(OC(=O)CCN[C:14](=[O:27])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:22][O:23][C:24](=[O:26])[N:25]=2)=[CH:17][CH:16]=1)C.O.[OH-].[Na+]>C1COCC1.CO>[O:23]1[C:24](=[O:26])[N:25]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:14]([OH:27])=[O:1])=[CH:20][CH:19]=2)[NH:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21866502OxadiazoloneHCID 178472065HCID 178472065, compound

Product 1

HCID 178524256HCID 178524256, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Cyanobenoic acid methyl ester (5.0 g, 31 mmol) was converted into the corresponding oxadiazolinone as described for the synthesis of compound 3. The crude product (4.6 g, 20.9 mmol) was dissolved in a mixture of THF (50 mL) and MeOH (50 mL). H2O (50 mL) was added, which gave a suspension, followed by 4 N aq. NaOH (10 mL). After 6 h the organic solvents were removed by distillation under reduced pressure. The aq. layer was extracted with EtOAc/toluene (1/2, v/v), acidified with 2 N hydrochloric acid and the precipitate was filtered off. The crude product was dried at 40° C. under reduced pressure to give 4.2 g (97%) of compound 60. ESI-MS: 207 [M+H]+.

Workup

  1. customwhich gave a suspension
  2. customAfter 6 h the organic solvents were removed by distillation under reduced pressure
  3. extractionThe aq. layer was extracted with EtOAc/toluene (1/2
  4. filtrationthe precipitate was filtered off
  5. dry with materialThe crude product was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-0e66850b06b44d9fb9f276013088a702
Source dataset
uspto-grants-2009_08
Patent number
US07576071B2

Reaction notes

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