Beta-Alanine → HCID 18795304, compound

HRID 580772Notes

Reaction equation

HRID 580772 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([C:10]([OH:12])=[O:11])[CH2:8][NH2:9].C(N(CC)CC)C.Cl>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([NH:9][CH2:8][CH2:7][C:10]([OH:12])=[O:11])=[O:4]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 18795304HCID 18795304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

72.69 g (311.3 mmol) of a-bromopropionic acid chloride is added in drops at 0° C. to 40 g (448.98 mmol) of b-alanine and 90 g (889.5 mmol) of triethylamine in 500 ml of methylene chloride. In this case, the temperature remains between 0° C.-5° C. 1000 ml of 5% aqueous hydrochloric acid is added, and the organic phase is separated. The organic phase is extracted once more with 500 ml of 5% aqueous hydrochloric acid, dried on magnesium sulfate and evaporated to dryness in a vacuum. The residue is recrystallized from acetone/diisopropyl ether.

Workup

  1. customremains between 0° C.-5° C
  2. customthe organic phase is separated
  3. extractionThe organic phase is extracted once more with 500 ml of 5% aqueous hydrochloric acid
  4. customdried on magnesium sulfate
  5. customevaporated to dryness in a vacuum
  6. customThe residue is recrystallized from acetone/diisopropyl ether

Sources & evidence

ORD record
ord-13efd572f0394af18453359e1930ee59
Source dataset
uspto-grants-1999_07
Patent number
US05919433

Reaction notes

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