Glycine ethyl ester → HCID 13813830, compound

HRID 1249244Notes

Reaction equation

HRID 1249244 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].Cl.C(OC(=O)CN)C>C(Cl)Cl>[Cl:7][CH2:6][C:2](=[O:1])[CH2:3][C:4]([NH:14][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:15])=[O:5]

Participants

6

Reactant 4

HCID 12176Glycine ethyl esterHCID 12661DiketeneHCID 24526ChlorineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 13813830HCID 13813830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 it for 1 h. The solution is then added rapidly dropwise to a solution of glycine ethyl ester prepared by suspending 9.30 g glycine ethyl ester hydrochloride in 160 ml methylene chloride containing 18.6 ml triethylamine, the mixture is stirred for 30 min and cooled to -30° C. Stirring is continued for 30 min, the solvent is evaporated in vacuo, and the residue taken up in ethyl acetate. The salts are filtered off, the solvent is evaporated and the residue chromatographed on silica, eluting with ethyl acetate. The compound is obtained as a white powder, m.p. 96°-7° C.

Workup

  1. customprepared
  2. temperaturecooled to -30° C
  3. stirringStirring
  4. waitis continued for 30 min
  5. customthe solvent is evaporated in vacuo
  6. filtrationThe salts are filtered off
  7. customthe solvent is evaporated
  8. customthe residue chromatographed on silica
  9. washeluting with ethyl acetate
  10. customThe compound is obtained as a white powder, m.p. 96°-7° C.

Sources & evidence

ORD record
ord-7353a310f87347c0ae3584a45a82e207
Source dataset
uspto-grants-1986_12
Patent number
US04629797

Reaction notes

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