Hydrochloric Acid → 3-(2-Amino-4-thiazolyl)-L-alanine methyl ester dihydrochloride

HRID 326408Notes

Reaction equation

HRID 326408 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.[ClH:13].[CH3:14]O>>[ClH:13].[ClH:13].[CH3:14][O:11][C:10](=[O:12])[C@H:8]([CH2:7][C:5]1[N:6]=[C:2]([NH2:1])[S:3][CH:4]=1)[NH2:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 111270113-(2-Amino-4-thiazolyl)alanine

Product 1

HCID 867454923-(2-Amino-4-thiazolyl)-L-alanine methyl ester dihydrochloride

Conditions

Temperature
5 °C

Procedure

3-(2-Amino-4-thiazolyl)-L alanine containing methanol, 26.3 kg (76 mol) and 72 L of methanol are charged into a reactor and stirred at 5° C., followed by 16.9 kg of anhydrous hydrogen chloride gas and stirred at 25° C. for 5 hours. The solution is heated to reflux and then cooled to 5° C. and held for 1 hour. The product is filtered and dried under vacuum at 50° C. to give 17.7 kg of 3-(2-amino-4-thiazolyl)-L-alanine methyl ester dihydrochloride as an off-white solid, 99% pure by HPLC; IR (mineral oil): 3410 (sh), 1749 (sh), 1631 (sh), 1225 (m) cm-1.

Workup

  1. additionare charged into a reactor
  2. stirringstirred at 25° C. for 5 hours
  3. temperatureThe solution is heated
  4. temperatureto reflux
  5. temperaturecooled to 5° C.
  6. filtrationThe product is filtered
  7. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-6dcf2a4916c94290a1708df05a454c0d
Source dataset
uspto-grants-1993_12
Patent number
US05268483

Reaction notes

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