Sodium Hydroxide → HCID 21075854, compound

HRID 1374152Notes

Reaction equation

HRID 1374152 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:4]=[N:3][CH:2]=1.[OH-].[Na+]>C1COCC1.O>[N:1]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21075874HCID 21075874, compound

Product 1

HCID 21075854HCID 21075854, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]cyclobutanecarboxylate (0.939 g, 3.77 mmol) was dissolved in THF (36.0 mL) prior to addition of aqueous sodium hydroxide (6.03 mL, 1M). The reaction mixture was then allowed to stir over the weekend (ca. 64 h) at ambient temperature. Most of the THF was then removed under reduced pressure to yield an oily aqueous layer, which was diluted with additional water, prior to three-fold extraction with diethyl ether. The aqueous layer was then made neutral by the addition of HCl (6.00 mL, 1H) and then saturated with sodium chloride. Repeated extraction of this aqueous layer with EtOAc (ca. 500 mL total) followed by concentration of the organic layers provided 1-[(pyrimidin-5-ylcarbonyl)-amino]cyclobutanecarboxylic acid (0.756 g) as a white solid giving proton NMR and LC/MS data consistent with theory.

Workup

  1. customMost of the THF was then removed under reduced pressure
  2. customto yield an oily aqueous layer, which
  3. extractionto three-fold extraction with diethyl ether
  4. additionThe aqueous layer was then made neutral by the addition of HCl (6.00 mL, 1H)
  5. extractionextraction of this aqueous layer with EtOAc (ca. 500 mL total)

Sources & evidence

ORD record
ord-9d80d8faee924459b9a86a2837f66be8
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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