Chloroform → HCID 86734138, compound

HRID 1729803Notes

Reaction equation

HRID 1729803 reaction equation
Cl.C([N:4]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])C.ClC(Cl)Cl.Cl[C:22]([O:24][CH3:25])=[O:23].[CH2:26](N(CC)CC)[CH3:27]>>[CH2:26]([CH:5]([CH2:6][C:7]([OH:9])=[O:8])[N:4]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:22]([O:24][CH3:25])=[O:23])[CH3:27]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86734135HCID 86734135, compound

Product 1

HCID 86734138HCID 86734138, compound

Procedure

To a stirred solution of 150 parts of ethyl N-[2-(ethoxycarbonyl)ethyl]-β-alanine hydrochloride in 1800 parts of trichloromethane are added 150 parts of N,N-diethylethanamine, while cooling. Then there are added dropwise 68 parts of methyl chloroformate. Upon completion, stirring is continued overnight at room temperature. The formed precipitate is filtered off and the filter-cake is washed with methylbenzene. The filtrate is evaporated and water is added to the residue. The product is extracted with methylbenzene. The extract is washed three times with water, dried, filtered and evaporated. The residue is distilled, yielding ethyl N-[2-(ethoxycarbonyl)ethyl]-N-(methoxycarbonyl)-β-alanine; bp. 137°-140° C at 0.2 mm. pressure.

Workup

  1. temperaturewhile cooling
  2. filtrationThe formed precipitate is filtered off
  3. washthe filter-cake is washed with methylbenzene
  4. customThe filtrate is evaporated
  5. additionwater is added to the residue
  6. extractionThe product is extracted with methylbenzene
  7. washThe extract is washed three times with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe residue is distilled

Sources & evidence

ORD record
ord-96e0e2bdb3324c33b0b0ad9deaf836e0
Source dataset
uspto-grants-1976_11
Patent number
US03989707

Reaction notes

Loading…