Hydrochloric Acid → HCID 18795312, compound

HRID 580775Notes

Reaction equation

HRID 580775 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].Cl.[C:7]([O:11][C:12](=[O:15])[CH2:13][NH2:14])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:7]([O:11][C:12](=[O:15])[CH2:13][NH:14][C:3](=[O:4])[CH2:2][Br:1])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 18795312HCID 18795312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

77.8 g (385.5 mmol) of α-bromoacetic acid bromide is added in drops at 0° C. to 50 g (296.5 mmol) of glycine-tert-butyl ester hydrochloride salt and 90 g (889.5 mmol) of triethylamine in 500 ml of methylene chloride. In this cases 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 diisopropyl ether/n-hexane.

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 diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-15360174d0da436abd16f7f7bb69c9a9
Source dataset
uspto-grants-1999_07
Patent number
US05919433

Reaction notes

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