Hydrochloric Acid → N-(Ethoxycarbonyl)alanine

HRID 258065Notes

Reaction equation

HRID 258065 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>O>[CH2:17]([O:16][C:14]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformate

Product 1

HCID 10558934N-(Ethoxycarbonyl)alanineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Production of 3-(methyl ONN azoxy)-2,2-propylene dioxy-butane [Compound (IV):R3 =H, R4 =-CH2CH2CH2 -]: (a) In 700 ml of water were dissolved 40 g of L-alanine and 127 g of sodium carbonate. Then 64 ml of ethyl chloroformate was added dropwise to the mixture under ice-cooling and its stirring was conducted at room temperature for 30 minutes. A 35% hydrochloric acid was added to the reaction liquid to make this acidic and the reaction liquid was adsorbed on the column (6.5×60 cm) of diaion HP-20. After washing with water this was eluted with 70% methanol. The eluate was condensed under vacuum thereby to obtain 69 g (yield of 96%) of N-ethoxycarbonyl alanine as an oily substance.

Workup

  1. temperaturecooling
  2. customthe reaction liquid
  3. washAfter washing with water
  4. washthis was eluted with 70% methanol
  5. customcondensed under vacuum

Sources & evidence

ORD record
ord-95fe1a3e930745e0ac73978f46fa9e67
Source dataset
uspto-grants-1993_11
Patent number
US05264559

Reaction notes

Loading…