Methanol → 3-(2-amino-4-thiazolyl)-L-alanine L-glutamic acid salt

HRID 326406Notes

Reaction equation

HRID 326406 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])[N:6]=1.[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18].CO>O>[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 33032L-Glutamic AcidHCID 111270113-(2-Amino-4-thiazolyl)alanine

Product 1

HCID 150281953-(2-amino-4-thiazolyl)-L-alanine L-glutamic acid salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

DL-3-(2-Amino-4-thiazolyl)alanine, 41.8 kg (223 mol) (Silberg, A., et al, Chemische Berichte, Vol. 97, pages 1767-69 (1964)) and 26.3 kg (179 mol) of L-glutamic acid are dissolved in 620 L of water at 60° C. Methanol (620 L) is added to the solution and the solution is cooled to 25° C. to crystallize the salt. After stirring for 2 to 3 hours at 25° C., the product is filtered and washed with 40 L of methanol. The product is dried at 40° C. under vacuum to give 37.6 kg of 3-(2-amino-4-thiazolyl)-L-alanine L-glutamic acid salt as a white solid. Infrared spectrum (IR) (mineral oil): 2927 (s, br), 1643 (s), 1605 (s), 1548 (s), 1407 (sh) cm-1.

Workup

  1. customto crystallize the salt
  2. filtrationthe product is filtered
  3. washwashed with 40 L of methanol
  4. customThe product is dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-12dc5448f6c04d40be0466b38261f8b2
Source dataset
uspto-grants-1993_12
Patent number
US05268483

Reaction notes

Loading…