Hydrochloric Acid → HCID 42633439, compound

HRID 2388239Notes

Reaction equation

HRID 2388239 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:18]3[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:20][O:21][C:17]=3[C:16]([OH:28])=[C:15]([C:29](OCC)=[O:30])[N:14]=2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:34][CH2:35][C:36]([OH:38])=[O:37].[O-]CC.[Na+].Cl>C(=O)(O)[O-].[Na+].CCOC(C)=O.O.CN(C=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:18]3[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:20][O:21][C:17]=3[C:16]([OH:28])=[C:15]([C:29]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:30])[N:14]=2)[N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67530374HCID 67530374, compound

Product 1

HCID 42633439HCID 42633439, compoundYield 85.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 4-(1-benzyl-1H-1,2,3-triazol-4-yl)-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (100 mg, 0.227 mmol), glycine (340 mg, 4.54 mmol) and sodium ethoxide (231 mg, 3.40 mmol) were added to 8 mL of DMF and the mixture was refluxed for 2 h. After the mixture was cooled to room temperature, water (50 mL) and EtOAc (50 mL) were added. The biphasic mixture was acidified to pH 2 by addition of 4M hydrochloric acid. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4 and concentrated to give an oily residue. The residue was dissolved in 300 mL of saturated sodium bicarbonate solution and washed with hexanes EtOAc. The aqueous layer was acidified with concentrated hydrochloric acid to pH 2 and extracted with EtOAc. The solvent was concentrated in vacuo to give 91 mg of the title compound. MS: (+) m/z 471.29 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give an oily residue
  6. washwashed with hexanes EtOAc
  7. extractionextracted with EtOAc
  8. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-c1a96ba6d70a495abda18e50ceb0bfbe
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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