1,4-Dioxane hydrochloride → (S)-2-Amino-N-methyl-3-thiazol-4-yl-propionamide hydrochloride

HRID 651105Notes

Reaction equation

HRID 651105 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:15](=[O:18])[NH:16][CH3:17])[CH2:9][C:10]1[N:11]=[CH:12][S:13][CH:14]=1)(C)(C)C.[ClH:20].O1CCOCC1>>[ClH:20].[NH2:7][C@@H:8]([CH2:9][C:10]1[N:11]=[CH:12][S:13][CH:14]=1)[C:15]([NH:16][CH3:17])=[O:18]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22850398(S)-(1-Methylcarbamoyl-2-thiazol-4-yl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 18395584(S)-2-Amino-N-methyl-3-thiazol-4-yl-propionamide hydrochloride

Conditions

Temperature
25 °C

Procedure

(S)-(1-Methylcarbamoyl-2-thiazol-4-yl-ethyl)-carbamic acid tert-butyl ester (248 mg, 0.87 mmol) was dissolved in 4 M HCl-dioxane at 0° C. The resulting mixture was stirred for 1 hour at 25° C., concentrated and the residue triturated with ether. Yield, 202 g, 102%; HPLC (70/30) 2.41 minutes (96%);

Workup

  1. concentrationconcentrated
  2. customthe residue triturated with ether
  3. customYield

Sources & evidence

ORD record
ord-050c6374028c422db4a125aa5bdaabad
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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