Sodium Carbonate → HCID 21284015, compound

HRID 1249239Notes

Reaction equation

HRID 1249239 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7]Br.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH2:20]>C(Cl)Cl>[Br:7][CH2:6][C:2](=[O:1])[CH2:3][C:4]([NH:20][CH2:19][C:18]([O:17][CH3:16])=[O:21])=[O:5]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 12661DiketeneHCID 24408BromineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 21284015HCID 21284015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

4.8 ml Diketene are dissolved in 30 ml methylene chloride. The solution is cooled to -50° C. and a solution of 3.24 ml bromine dissolved in 20 ml methylene chloride is added dropwise over 30 min. The mixture is left stirring for 2 h at ambient temperature. At -40° is added, all at once, an intimate mixture of 20 g finely ground Na2CO3 and 7.9 g glycine methyl ester hydrochloride. Stirring is continued for 90 min, allowing the mixture to return to ambient temperature. The salt is filtered quickly, the filtrate is concentrated in vacuo at ambient temperature. The residual oil is purified by chromatography on silica, eluting with ethyl acetate. The desired compound is obtained as a white powder, m.p. 76°-77° C.

Workup

  1. additionis added dropwise over 30 min
  2. waitThe mixture is left
  3. additionAt -40° is added
  4. stirringStirring
  5. waitis continued for 90 min
  6. customto return to ambient temperature
  7. filtrationThe salt is filtered quickly
  8. concentrationthe filtrate is concentrated in vacuo at ambient temperature
  9. customThe residual oil is purified by chromatography on silica
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5eb184ffcf454416a28b120a6521adcf
Source dataset
uspto-grants-1986_12
Patent number
US04629797

Reaction notes

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