Hydrochloric Acid → HCID 21117230, compound

HRID 580773Notes

Reaction equation

HRID 580773 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C@H:8]([C:10]([OH:12])=[O:11])[CH3:9].C(N(CC)CC)C.Cl>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([NH:7][C@H:8]([C:10]([OH:12])=[O:11])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 8471TriethylamineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 21117230HCID 21117230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

69.26 g (404 mmol) of α-bromopropionic acid chloride is added in drops at 0° C. to 30 g (336.7 mmol) of alanine and 102.2 g (1010.2 mmol) of triethylamine in 600 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 400 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 400 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-1e958d29bbb54188b811c73c49a45bb7
Source dataset
uspto-grants-1999_07
Patent number
US05919433

Reaction notes

Loading…