Glycine → {[3-(4-Fluoro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carbonyl]-amino}-acetic acid

HRID 1847240Notes

Reaction equation

HRID 1847240 reaction equation
C(O[C:4]([C:6]1[C:7]([OH:22])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[N:13][S:12][C:9]2=[CH:10][N:11]=1)=[O:5])C.[NH2:23][CH2:24][C:25]([OH:27])=[O:26].C[O-].[Na+]>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2[C:8]3[C:9](=[CH:10][N:11]=[C:6]([C:4]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:5])[C:7]=3[OH:22])[S:12][N:13]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 1363440103-(4-Fluoro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 135870679{[3-(4-Fluoro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carbonyl]-amino}-acetic acidYield 89.4%

Procedure

A mixture of 3-(4-Fluoro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (150 mg, 0.47 mmol), glycine (1.06 g, 14.1 mmol), and NaOMe (23.5 mL, 11.75 mmol, 0.5 M solution in MeOH) was refluxed for 24 h. After cooling to r.t. the mixture was concentrated in vacuo. The residue was dissolved in water (50 mL), and the solution washed with CH2Cl2 (2×30 mL) before it was acidified by addition of aqueous 1N HCl solution. The resulting precipitate was sucked off, washed with water, and dried in vacuo to give the title compound (146 mg) as white solid: MS (m/z) 346.1 (M−1)+.

Workup

  1. temperaturewas refluxed for 24 h
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in water (50 mL)
  4. washthe solution washed with CH2Cl2 (2×30 mL) before it
  5. additionwas acidified by addition of aqueous 1N HCl solution
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-dfb2a146d05a451bb9f03a01c7c2142e
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

Loading…