Hydrochloric Acid → HCID 57554678, compound

HRID 1511898Notes

Reaction equation

HRID 1511898 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:25][C:18]3([NH:22]C(=O)N[C:19]3=[O:24])[CH2:17][O:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-:26].[Na+].Cl>O>[NH2:22][C:18]1([C:19]([OH:24])=[O:26])[CH2:25][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)[O:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57554771HCID 57554771, compound

Product 1

HCID 57554678HCID 57554678, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

8-(4-Octylphenyl)-7-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (0.5 g, 1.452 mmol) and sodium hydroxide (10.89 ml, 21.77 mmol) were combined in water (8.54 ml) and equipped with a reflux condensor. The mixture was heated at about 100° C. for about 72 h. The reaction was cooled and acidified with concentrated HCl until pH=4-5. The product was collected by vacuum filtration and dried under vacuum. The residue was purified by flash column chromatography (1″×6″ of silica) eluting with 1:1 EtOAc/(6:3:1 CHCl3/MeOH/NH4OH). The product fractions were combined. The solvents were removed under reduced pressure and the residue triturated with ether. The resulting solid was collected by vacuum filtration and washed with ether to provide 3-amino-5-(4-octylphenyl)tetrahydrofuran-3-carboxylic acid (0.280 g, 0.877 mmol, 60.4% yield) as a white solid:

Workup

  1. customequipped with a reflux condensor
  2. temperatureThe reaction was cooled
  3. filtrationThe product was collected by vacuum filtration
  4. customdried under vacuum
  5. customThe residue was purified by flash column chromatography (1″×6″ of silica)
  6. washeluting with 1:1 EtOAc/(6:3:1 CHCl3/MeOH/NH4OH)
  7. customThe solvents were removed under reduced pressure
  8. customthe residue triturated with ether
  9. filtrationThe resulting solid was collected by vacuum filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-c0fd3b1a655840ceaa211b2f18f24cc7
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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