Hydrochloric Acid → L-Alanine, ethyl ester, hydrochloride (1:1)

HRID 2392822Notes

Reaction equation

HRID 2392822 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:5]([OH:7])=[O:6])[CH3:4].[CH2:8](O)[CH3:9]>>[ClH:1].[CH2:8]([O:6][C:5](=[O:7])[C@H:3]([CH3:4])[NH2:2])[CH3:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5950L-Alanine

Product 1

HCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Procedure

Hydrogen chloride gas was bubbled into a suspension of L-alanine (1) (100 g, 1.12 mol) in dry ethanol (800 ml) and the solution was refluxed for 2 hours. After concentration in vacuo the compound was recrystallised from ethanol-diethyl ether giving the title ester (2) (168.2g, 98%) as a white solid. δH (200 MHz; D2O) 1.11 (3H, t, J=7.1, CH2 CH3), 1.37 (3H, d, J=7.4, CHCH3), 4.03 (1H, q, J=7.2, CHCH3), 4.09 (2H, q, J=7.2, CH2CH3), 4.16 (2H, s, NH2); δC (125 MHz; D2O) 13.98 (CH3), 15.90 (CH3), 49.65 (CH), 64.29 (CH2), 171.57 (CO).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. concentrationAfter concentration in vacuo the compound
  3. customwas recrystallised from ethanol-diethyl ether giving the title ester (2) (168.2g, 98%) as a white solid

Sources & evidence

ORD record
ord-07dfd79cb225455e925f74527d536dc3
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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