Beta-Alanine → 3-(Cyclohexylformamido)propanoic acid

HRID 1428419Notes

Reaction equation

HRID 1428419 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[CH:9]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>O>[CH:9]1([C:15]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 119834713-(Cyclohexylformamido)propanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ten grams of β-alanine and 9 g of sodium hydroxide were dissolved in 100 mL of purified water, and 14.9 g of cyclohexanecarbonyl chloride were added dropwise under freezing conditions. After stirring for five hours, hydrochloric acid was added and the pH was adjusted to 2 or less. After extraction with 500 mL of ethyl acetate, the product was desiccated over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was recrystallized with aqueous ethanol, and 17.2 g of the desired product was obtained (yield of 85%).

Workup

  1. extractionAfter extraction with 500 mL of ethyl acetate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was recrystallized with aqueous ethanol

Sources & evidence

ORD record
ord-7123eef2ed094a5e80f4dfc4d6e1b5a9
Source dataset
uspto-grants-2015_01
Patent number
US08937090B2

Reaction notes

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