Reaction #816389

Reaction equation

glycine benzylester hydrochloride

K2CO3

chloroacetylchloride

→

material 1

N-(chloroacetyl)-glycine benzyl ester

Solvents

CH2Cl2

H2O

Conditions

Workup

1. 1
   TemperatureThe mixture was warmed to room temperature
2. 2
   OtherThe two layers were separated
3. 3
   Extractionthe aqueous layer was extracted with CH2Cl2 (100 ml)
4. 4
   Washwashed with H2O (100 ml), brine (100 ml)
5. 5
   Dryingdried (MgSO4)
6. 6
   OtherEvaporation of solvent
7. 7
   Otherafforded a light yellowish glassy solid
8. 8
   OtherThis was triturated with 250 ml of hexane
9. 9
   OtherThe colorless solid was collected
10. 10
    Otherdried

Procedure

To a suspension of glycine benzylester hydrochloride (25.2 g, 12.5 mmol, Aldrich) in CH2Cl2 (200 ml) was added a solution of K2CO3 (77 g, 55.8 mmol) in H2O (200 ml). The mixture was cooled to 0° C. and chloroacetylchloride (21.0 g, 18.6 mol, Aldrich) was added dropwise in 15 min. The mixture was warmed to room temperature and stirred for 2 h. The two layers were separated and the aqueous layer was extracted with CH2Cl2 (100 ml). The organic layers were combined and washed with H2O (100 ml), brine (100 ml), dried (MgSO4). Evaporation of solvent afforded a light yellowish glassy solid. This was triturated with 250 ml of hexane. The colorless solid was collected and dried to give 30.0 g of the material 1.

Source