Glycine → Glycine, N-[(2,2,2-trichloroethoxy)carbonyl]-

HRID 2083805Notes

Reaction equation

HRID 2083805 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[NH2:10][CH2:11][C:12]([OH:14])=[O:13]>[OH-].[Na+]>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 750GlycineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 11139569Glycine, N-[(2,2,2-trichloroethoxy)carbonyl]-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

2,2,2-Trichloroethyl chloroformate (23,30 g, 0.11 mole) and 4N NaOH (30 ml, 0.12 mole) are added alternately in about 5 equal portions over a period of 30 minutes to an ice-cold, vigorously stirring solution of glycine (7.51 g, 0.1 mole) in 4N NaOH (25 ml). Upon completion of the reaction, the solution is extracted with ether, and the aqueous portion is slurried with EtOAc and acidified in the cold to pH 2.5 with 6N HCl. The EtOAc solution is separated, washed with H2O, dried over MgSO4, filtered, and evaporated in vacuo to give N-(2,2,2-trichloroethyloxycarbonyl)-glycine.

Workup

  1. customUpon completion of the reaction
  2. extractionthe solution is extracted with ether
  3. customThe EtOAc solution is separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-1804ef678841471aa61aa1e06f146729
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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