Hydrochloric Acid → {[4-Cyano-7-hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

HRID 2388215Notes

Reaction equation

HRID 2388215 reaction equation
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:20])=[C:5]([C:21](OCC)=[O:22])[N:4]=1)#[N:2].[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].Cl>C(=O)(O)[O-].[Na+]>[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:20])=[C:5]([C:21]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:22])[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium MethoxideHCID 67530678Ethyl 4-cyano-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

Product 1

HCID 42633241{[4-Cyano-7-hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acidYield 71.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 4-cyano-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (86 mg, 0.254 mmol) and glycine (381 mg, 5.07 mmol) were added to sodium methoxide solution (7.6 mL, 3.80 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 75 mg of crude solid. The solid was dissolved in 200 mL of saturated sodium bicarbonate solution and washed with EtOAc. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and the precipitate was collected by filtration. The solid was dried under vacuum to afford 67 mg of the title compound. MS: (−) m/z 367.34 (M−1).

Workup

  1. temperaturethe mixture was refluxed for 3 days
  2. customThe precipitate was isolated by filtration
  3. customdried under vacuum
  4. customto give 75 mg of crude solid
  5. washwashed with EtOAc
  6. filtrationthe precipitate was collected by filtration
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-d67c48c49add4598ace66c61c529fc46
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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