1,4-Dioxane → 4-Amino-3-methyl-1,2-thiazole-5-carboxylic acid

HRID 1782156Notes

Reaction equation

HRID 1782156 reaction equation
C(OC([NH:8][C:9]1[C:10]([CH3:17])=[N:11][S:12][C:13]=1[C:14]([OH:16])=[O:15])=O)(C)(C)C.O1CCOCC1>Cl>[NH2:8][C:9]1[C:10]([CH3:17])=[N:11][S:12][C:13]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 547572143-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2-thiazole-5-carboxylic acid, 4-tert-Butoxycarbonylamino-3-methyl-isothiazole-5-carboxylic acid

Product 1

HCID 228318524-Amino-3-methyl-1,2-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-tert-Butoxycarbonylamino-3-methyl-isothiazole-5-carboxylic acid (method 56) (11 g, 45 mmol) was dissolved in 50 mL of 4M solution of HCl in 1,4-dioxane (200 mmol) and the resulting solution was stirred at room temperature overnight. The TLC showed the complete disappearance of the starting acid. The reaction was concentrated and the residue was triturated with ether and the precipitated hydrochloride salt was filtered off and washed with ether and dried to provide the product as a light brown powder. Yield 8.2 g (100%). 1H NMR (300 MHz, DMSO-d6) δ 2.30 (s, 3H), 8.85 (bs, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was triturated with ether
  3. filtrationthe precipitated hydrochloride salt was filtered off
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-e7dc112e99194e489a6f48d4466c973a
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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