Methanol → 3-(2-Amino-4-thiazolyl)alanine

HRID 326407Notes

Reaction equation

HRID 326407 reaction equation
N[C@H](C(O)=O)CCC(O)=O.[NH2:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[N:16]=1.CO>C(N(CC)CC)C>[NH2:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])[N:16]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 150281953-(2-amino-4-thiazolyl)-L-alanine L-glutamic acid salt

Product 1

HCID 111270113-(2-Amino-4-thiazolyl)alanine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

3-(2-Amino-4-thiazolyl)-L-alanine L-glutamic acid salt, 37.6 kg (112 mol) and 420 L of methanol are charged into a reactor and stirred as 34.4 kg of triethylamine is added. The slurry is heated to reflux for 1 hour and then cooled to 5° C. The product is filtered, washed with 25 L of methanol to give 26.3 kg of 3-(2 amino-4-thiazolyl)-L-alanine as a white solid containing methanol. A dried sample is >99% pure and >99% enantiomeric excess by chiral high pressure liquid chromatography (HPLC); IR (mineral oil): 3170 (s, br), 1618 (s), 1525 (s), 1108 (m) cm-1.

Workup

  1. additionis added
  2. temperatureThe slurry is heated
  3. temperatureto reflux for 1 hour
  4. filtrationThe product is filtered
  5. washwashed with 25 L of methanol

Sources & evidence

ORD record
ord-877370edc1444e5cb9197a86701033a5
Source dataset
uspto-grants-1993_12
Patent number
US05268483

Reaction notes

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