Alpha-Aminobutyric Acid → HCID 86761141, compound

HRID 2355656Notes

Reaction equation

HRID 2355656 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH2:6][CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9]>C1COCC1>[Br:1][CH2:2][C:3]([NH:6][CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 6657Alpha-Aminobutyric AcidHCID 61147Bromoacetyl bromide

Product 1

HCID 86761141HCID 86761141, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of bromoacetyl bromide (50 g, 24 mmol 1 molar eq.) in dry THF (500 ml) was slowly added to a 2 L round-bottomed three-neck flask with a mechanical stirrer, a nitrogen gas purge and an addition funnel containing 2-aminobutyric acid (25 g, 24 mmol) in 500 mL dry THF. After stirring at room temperature for 12 hours the reaction mixture was filtered and the THF evaporated from the filtrate gave yellow oil, which crystallized upon cooling in 60% yield. 1H NMR (500 MHz, DMSO d6) δ (ppm): 8.30 (s, 1H), 3.8 (s, 2H), 1.5 (s, 6H). 13C NMR (500 MHz, DMSO d6) δ (ppm): 178, 177, 57, 29, 25. MS (m/z) (%) 224 (30), 208 (20), 178 (99), 121 (40), 88 (65), 58 (100).

Workup

  1. customa nitrogen gas purge
  2. filtrationwas filtered
  3. customthe THF evaporated from the filtrate
  4. customgave yellow oil, which
  5. customcrystallized
  6. temperatureupon cooling in 60% yield

Sources & evidence

ORD record
ord-cc8c157c7ae94d88923581ed4e74ef67
Source dataset
uspto-grants-2010_07
Patent number
US07754826B1

Reaction notes

Loading…