Hydrochloric Acid → Methyl 2-(aminomethyl)-1,3-thiazole-4-carboxylate

HRID 1009197Notes

Reaction equation

HRID 1009197 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11]C(OC(C)(C)C)=O)[S:8][CH:9]=1)=[O:4].Cl>CO.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH2:11])[S:8][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9816939HCID 9816939, compound

Product 1

HCID 24274654Methyl 2-(aminomethyl)-1,3-thiazole-4-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(tert-Butoxycarbonylamino-methyl)-thiazole-4-carboxylic acid methyl ester (1.1 g, 3.9 mmol) was dissolved in methanol (15 mL). HCl in dioxane (4 M, 5 mL) was added. The mixture was stirred for 12 hours. The mixture was concentrated in vacuo, re-dissolved in methanol, and stirred with Bio-RAD AG 1-X8 resin (4 g, 20-50 mesh, hydroxide form, pre-washed with methanol and air dried) for 35 min. The mixture was filtered and the filtrate was concentrated in vacuo to afford the title compound (0.48 g, 73% over two steps): 1H NMR (400 MHz, d6-DMSO): 8.38 (s, 1H), 3.97 (s, 2H), 3.80 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionre-dissolved in methanol
  3. stirringstirred with Bio-RAD AG
  4. washresin (4 g, 20-50 mesh, hydroxide form, pre-washed with methanol and air dried) for 35 min
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f9a8a7a9a73a439cb160627d8ed0bd7a
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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