Glycine → [(4-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acid

HRID 642373Notes

Reaction equation

HRID 642373 reaction equation
C(O[C:4]([C:6]1[N:11]=[C:10]([Br:12])[C:9]2[S:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:15][C:8]=2[C:7]=1[OH:22])=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26]>C[O-].[Na+].CO>[Br:12][C:10]1[C:9]2[S:13][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:15][C:8]=2[C:7]([OH:22])=[C:6]([C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5])[N:11]=1

Participants

4

Reactant 2

HCID 750GlycineHCID 866173574-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 86617359[(4-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carbonyl)-amino]-acetic acidYield 67.1%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (191 mg, 0.50 mmole) and glycine (1.33 g, 17.69 mmole) in 0.5 M sodium methoxide/methanol (25.3 ml) was refluxed for 28 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (120 ml) and extracted with dichloromethane (3×100 ml). The remaining aqueous layer was acidified to pH=2 with 1N HCl. The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a yellow solid (137 mg). MS: (+) m/z 408.12, 410.09 (M+1, 79Br/8tBr), (−) m/z 406.08, 408.05 (M−1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 28 h before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (120 ml)
  4. extractionextracted with dichloromethane (3×100 ml)
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-35d337f7ce034e11b8f437629e20512e
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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