Hydrochloric Acid → HCID 11309757, compound

HRID 2247149Notes

Reaction equation

HRID 2247149 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[CH2:15](Br)[CH:16]=[CH2:17].Cl.[CH2:20]1[CH2:24]OC[CH2:21]1>>[CH3:2][O:3][C:4](=[O:7])[CH2:5][N:6]([CH2:24][CH:20]=[CH2:21])[CH2:15][CH:16]=[CH2:17]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 11309757HCID 11309757, compoundYield 49%

Procedure

1.5 g (11.9 mmole) glycine methylester hydrochloride was added to 100 ml dry THF and subsequently, 3.61 g (35.8 mmole) triethylamine was added. After 15 minutes stirring at room temperature, 4.33 g (35.8 mmole) allyl bromide was added dropwise and the mixture was refluxed for 16 hours. 100 ml of 2N HCl was added and then extracted with 100 ml diethyl ether. The aqueous phase was alkalinised after, acid extraction, with K2CO3 and extracted with CH2Cl2 (100 ml three times). The organic layer was dried with MgSO4. The product was further purified, after filtration of MgSO4 and evaporation of the solvent, via column chromatography, providing with 100% selectivity 0.78 g (5.75 mmole, yield 49%) diallylglycine methyl ester. This product was further characterised by the following spectra:

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. extractionextracted with 100 ml diethyl ether
  3. extractionacid extraction
  4. extractionwith K2CO3 and extracted with CH2Cl2 (100 ml three times)
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationafter filtration of MgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-63d68b7162e848c682c34ef2edfdacf1
Source dataset
uspto-grants-2010_03
Patent number
US07687635B2

Reaction notes

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