Water → HCID 42633437, compound

HRID 2388232Notes

Reaction equation

HRID 2388232 reaction equation
[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:18])=[C:5]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[N:4]=1)#[CH:2].[OH2:26]>C1COCC1.OS(O)(=O)=O.[Cl-].[Na+].O.C(=O)(O)[O-].[Na+]>[C:1]([C:3]1[C:8]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][O:11][C:7]=2[C:6]([OH:18])=[C:5]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[N:4]=1)(=[O:26])[CH3:2]

Participants

7

Reactant 2

HCID 962WaterHCID 42633246HCID 42633246, compound

Product 1

HCID 42633437HCID 42633437, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(4-ethynyl-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxamido)acetic acid (60 mg, 0.178 mmol) was dissolved in 6.6 mL of THF. Water (0.7 mL) was added, followed by 1.5 mL of a saturated solution of HgSO4 in 1% H2SO4. The reaction mixture was stirred at room temperature for 16 h. Brine (10 mL) was added and the mixture was extracted with EtOAc. The combined organic layer was dried over MgSO4 and concentrated to give a purple solid. The solid was taken up in 25 mL of saturated sodium bicarbonate solution and washed several times with EtOAc. The aqueous layer was acidified to pH 3 with 4M hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 65 mg of crude solid. The solid was purified by flash chromatography (0-100% EA/hexanes+2% acetic acid) to give 20 mg of the title compound. MS: (−) m/z 354.22 (M−1).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto give a purple solid
  5. washwashed several times with EtOAc
  6. extractionextracted with EtOAc
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customto give 65 mg of crude solid
  10. customThe solid was purified by flash chromatography (0-100% EA/hexanes+2% acetic acid)

Sources & evidence

ORD record
ord-cd1bb9aeea594cecbfbde8bc03a51207
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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