Glycine ethyl ester → HCID 13813833, compound
Reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Cl:7]Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10]>C(Cl)Cl>[Cl:7][CH2:1][CH:2]([OH:6])[CH2:3][C:4]([NH:14][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:15])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
5.08 ml diketene are dissolved in 40 ml CH2Cl2. The solution is cooled to -30° C. and chlorine is passed through for 90 min. The solution is then added rapidly dropwise to a solution of glycine ethyl ester in 160 ml CH2Cl2 prepared as in the preceding example. After stirring for 30 min, the solvent is evaporated in vacuo, the residue is taken up in ethyl acetate and the salts filtered off. The solvent is evaporated, the oily residue is dissolved in 150 ml ethanol, cooled in ice, and 1.26 g NaBH4 is added in portions. After 30 min a few drops of dilute hydrochloric acid are added, the solvent is evaporated, the residue is taken up in ethyl acetate, washed with brine and dried. The solvent is evaporated and the residue chromatographed on silica, eluting with ethyl acetate. The compound is obtained as a white powder, m.p. 53°-4° C.
Workup
- customis passed through for 90 min
- customthe solvent is evaporated in vacuo
- filtrationthe salts filtered off
- customThe solvent is evaporated
- dissolutionthe oily residue is dissolved in 150 ml ethanol
- temperaturecooled in ice
- addition1.26 g NaBH4 is added in portions
- additionAfter 30 min a few drops of dilute hydrochloric acid are added
- customthe solvent is evaporated
- washwashed with brine
- customdried
- customThe solvent is evaporated
- customthe residue chromatographed on silica
- washeluting with ethyl acetate
- customThe compound is obtained as a white powder, m.p. 53°-4° C.
Sources & evidence
- ORD record
- ord-eac60a8c6a2d421b872b4cd3df580e3e
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04629797
Reaction notes
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