Ethyl Acetate → HCID 21949644, compound

HRID 2215215Notes

Reaction equation

HRID 2215215 reaction equation
C([O:3][C:4](=[O:16])[CH:5]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH:7]=[CH2:8])C.[OH-].[Na+].CCOC(C)=O>CCO.C1COCC1>[CH3:12][C:11]([CH3:14])([CH3:13])[C:10]([NH:9][CH:5]([CH2:6][CH:7]=[CH2:8])[C:4]([OH:16])=[O:3])=[O:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 85970119HCID 85970119, compound

Product 1

HCID 21949644HCID 21949644, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10.50 g of the above prepared 2-(2,2-dimethyl-propionylamino)-pent-4-enoic acid ethyl ester (46.19 mmol) were dissolved in 146 ml of a 1:1 mixture of EtOH and THF and treated under cooling with an ice bath with 46.19 ml of 2N NaOH (2 eq.). After 1 h, the reaction mixture was poured onto crashed ice/AcOEt/HCl, the aqueous phase reextracted once more with AcOEt, the combined organic layers washed with water, dried over sodium sulfate, and evaporated to dryness. Thereby, 8.45 g of the title product was obtained as white solid of mp. 87–88°.

Workup

  1. additiontreated
  2. additionthe reaction mixture was poured
  3. washthe combined organic layers washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-da061cb392cb420cb58058d6415d325c
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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