Water → 3-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acrylic acid

HRID 366180Notes

Reaction equation

HRID 366180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 10729697tert-Butyl 3-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]azetidine-1-carboxylate

Product 1

HCID 107993123-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acrylic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-((E)-2-Ethoxycarbonylvinyl)azetidine-1-carboxylic acid tert-butyl ester (0.95 g; 3.72 mmol) was dissolved in 1,4-dioxane (15 mL). Lithium hydroxide (0.098 g; 4.1 mmol) and water (10 mL) were added. The reaction mixture was stirred for 12 hours at room temperature. Water (70 mL) was added and the reaction mixture was washed with tert-butyl methyl ether (70 mL) and the phases were separated. The aqueous phase was adjusted to pH 2 with an aqueous solution of sodium hydrogensulfate (10%) and extracted with tert-butyl methylether (3×70 mL). The combined organic phases were dried (magnesium sulfate) and the solvent evaporated in vacuo to afford 0.76 g of 3-((E)-2-carboxyvinyl)azetidine-1-carboxylic acid tert-butyl ester.

Workup

  1. washthe reaction mixture was washed with tert-butyl methyl ether (70 mL)
  2. customthe phases were separated
  3. extractionextracted with tert-butyl methylether (3×70 mL)
  4. dry with materialThe combined organic phases were dried (magnesium sulfate)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1a269a6fed9a4d3783b5f3bd376f48d7
Source dataset
uspto-grants-2000_10
Patent number
US06127391

Reaction notes

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