Glycine → HCID 42633247, compound

HRID 2388227Notes

Reaction equation

HRID 2388227 reaction equation
[CH:1]1([C:4]2[C:9]3[C:10]([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)=[N:11][O:12][C:8]=3[C:7]([OH:18])=[C:6]([C:19](OCC)=[O:20])[N:5]=2)[CH2:3][CH2:2]1.[NH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[CH:1]1([C:4]2[C:9]3[C:10]([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)=[N:11][O:12][C:8]=3[C:7]([OH:18])=[C:6]([C:19]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:20])[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 750GlycineHCID 10942334Sodium MethoxideHCID 67531314HCID 67531314, compound

Product 1

HCID 42633247HCID 42633247, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 4-cyclopropyl-7-hydroxy-3-(thiophen-2-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (47 mg, 0.142 mmol) and glycine (428 mg, 5.70 mmol) were added to sodium methoxide solution (8.5 mL, 4.27 mmol, 0.5 M in MeOH) and the mixture was refluxed for 48 h. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was redissolved in 10 mL of water and acidified to pH 3 by addition of concentrated hydrochloric acid. The resulting precipitate was isolated by filtration to give 51 mg of crude solid. The solid was dissolved in saturated sodium bicarbonate (20 mL), and washed with EtOAc. The aqueous layer was acidified to pH 3 with 4M HCl and extracted with EtOAc. The combined organic layer was dried over MgSO4 and concentrated to give 36 mg of the title compound. MS: (−) m/z 358.30 (M−1).

Workup

  1. temperaturethe mixture was refluxed for 48 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was redissolved in 10 mL of water
  4. additionacidified to pH 3 by addition of concentrated hydrochloric acid
  5. customThe resulting precipitate was isolated by filtration
  6. customto give 51 mg of crude solid
  7. washwashed with EtOAc
  8. extractionextracted with EtOAc
  9. dry with materialThe combined organic layer was dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e203a062965e40e4a0c70737afb32d37
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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