Trifluoroacetic acid → 2-Amino-thiazole-4-carboxylic acid methoxy-methyl-amide

HRID 2222988Notes

Reaction equation

HRID 2222988 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:18])[N:14]([O:16][CH3:17])[CH3:15])[N:12]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:17][O:16][N:14]([CH3:15])[C:13]([C:11]1[N:12]=[C:8]([NH2:7])[S:9][CH:10]=1)=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58604314tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate

Product 1

HCID 627870592-Amino-thiazole-4-carboxylic acid methoxy-methyl-amideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (1.0 g, 3.48 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (5.0 mL, 64.9 mmol) at 0° C. The reaction was warmed to ambient temperature and stirred for 4 hours. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate and the organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was removed to give 2-amino-thiazole-4-carboxylic acid methoxy-methyl-amide as a foam (585 mg, 90%).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-5420f87298564fd7b0c285b40b8f310a
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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