Hydrochloric Acid → HCID 18795302, compound

HRID 1003140Notes

Reaction equation

HRID 1003140 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].C(N(CC)CC)C.Cl>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1708311-Aminoundecanoic acidHCID 979802-Bromopropanoyl chloride

Product 1

HCID 18795302HCID 18795302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30.65 g (178.8 mmol) of α-bromopropionic acid chloride is added in drops at 0° C. to 30 g (149 mmol) of 11-aminoundecanoic acid and 45.24 g (447.1 mmol) of triethylamine in 600 ml of methylene chloride. In this case, the temperature remains between 0° C.-5° C. 800 ml of 5% aqueous hydrochloric acid is added, and the organic phase is separated. The organic phase is extracted once more with 300 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 300 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-87472a02d9b1465f818b21419f2db852
Source dataset
uspto-grants-2000_04
Patent number
US06045776

Reaction notes

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