Ethyl Acetate → HCID 21949603, compound

HRID 2215253Notes

Reaction equation

HRID 2215253 reaction equation
C([O:3][C:4](=[O:15])[CH:5]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[CH2:6][CH:7]=[CH2:8])C.[OH-].[Na+].CCOC(C)=O>CCO.C1COCC1>[C:10]([NH:9][CH:5]([CH2:6][CH:7]=[CH2:8])[C:4]([OH:15])=[O:3])(=[O:14])[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 85970139HCID 85970139, compound

Product 1

HCID 21949603HCID 21949603, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.70 g of the above prepared 2-isobutyrylamino-pent-4-enoic acid ethyl ester (67.55 mmol) were dissolved in 110 ml of a 1:1 mixture of EtOH and THF and treated under cooling with an ice bath with 33.80 ml of 2N NaOH (2 eq.). After 2.5 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 and brine, dried over magnesium sulfate, and evaporated to dryness. Crystallization from AcOEt/hexane afforded 7.95 g of the title product as white solid.

Workup

  1. additiontreated
  2. additionthe reaction mixture was poured
  3. washthe combined organic layers washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-3273f0d195274bf7b90df5b267733779
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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