Hydrochloric Acid → N-(Chloroacetyl)glycylglycylglycine

HRID 1723454Notes

Reaction equation

HRID 1723454 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4].[Cl:14][CH2:15][C:16](Cl)=[O:17].Cl>[OH-].[Na+].CCOCC>[Cl:14][CH2:15][C:16]([NH:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[O:4])=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 11161Glycylglycylglycine

Product 1

HCID 14723669N-(Chloroacetyl)glycylglycylglycine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a stirred solution of 2.5 g (0.013 mol) of glycylglycylglycine in 75 ml of 1.0N NaOH in a 500 ml flask under nitrogen at 0° C., a solution of 13.0 g (0.115 mol) of chloroacetyl chloride in 100 ml of ether was added dropwise from one addition funnel while simultaneously 100 ml of 1.0N NaOH was added dropwise from another. After additions were complete, the reaction mixture was stirred for 1.5 hr. at 0° C. The mixture was then acidified with concentrated HCl while cooling. After stirring for an additional 30 min. the mixture was concentrated to one-third volume under reduced pressure at 40° C. The residue precipitated upon cooling in an ice bath. Isolation of the solid gave 2.75 g (78.5%) after two washings.

Workup

  1. additionwas added dropwise from another
  2. customat 0° C
  3. temperaturewhile cooling
  4. stirringAfter stirring for an additional 30 min. the mixture
  5. concentrationwas concentrated to one-third volume under reduced pressure at 40° C
  6. customThe residue precipitated
  7. temperatureupon cooling in an ice bath
  8. customIsolation of the solid gave 2.75 g (78.5%) after two washings

Sources & evidence

ORD record
ord-ec4551d39abd4a9ebebf3fc4e302aea9
Source dataset
uspto-grants-1989_08
Patent number
US04861869

Reaction notes

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