Beta-Alanine → HCID 11096866, compound

HRID 411958Notes

Reaction equation

HRID 411958 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].Cl[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:9].Cl>[OH-].[Na+]>[CH2:11]([O:10][C:8]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 81956Carbonochloridic acid, octyl ester

Product 1

HCID 11096866HCID 11096866, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

20 g (224.46 mmol) of β-alanine were dissolved in 225 ml of 1N sodium hydroxide solution. 44 ml of octyl chloroformate were then added dropwise, while keeping the pH of the reaction medium above 9 by simultaneous addition of one molar equivalent of 1N sodium hydroxide. After stirring for 6 hours at room temperature, the mixture was acidified with about 1.1 molar equivalents of 3N hydrochloric acid solution. The heterogeneous mixture was extracted with 300 ml of ethyl acetate. The organic phase was washed with 3 times 80 ml of water, dried and then evaporated to dryness. The solid residue was taken up in heptane and then filtered and dried. 51 g of a white product were obtained (yield of 93%).

Workup

  1. extractionThe heterogeneous mixture was extracted with 300 ml of ethyl acetate
  2. washThe organic phase was washed with 3 times 80 ml of water
  3. customdried
  4. customevaporated to dryness
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-cf36072c257048b99d28f8a616fd25a5
Source dataset
uspto-grants-2003_05
Patent number
US06562789B2

Reaction notes

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