Hydrochloric Acid → HCID 54133002, compound

HRID 580774Notes

Reaction equation

HRID 580774 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10].C(N(CC)CC)C.Cl>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([NH:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6287L-ValineHCID 8471TriethylamineHCID 979802-Bromopropanoyl chloride

Product 1

HCID 54133002HCID 54133002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70.2 g (409.7 mmol) of a-bromopropionic acid chloride is added in drops at 0° C. to 40 g (341.4 mmol) of valine and 103.7 g (1024 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 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 The residue
  6. customis recrystallized from acetone/diisopropyl ether

Sources & evidence

ORD record
ord-f86e61b7bf5742e8b44d398800df4783
Source dataset
uspto-grants-1999_07
Patent number
US05919433

Reaction notes

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