Hydrochloric Acid → HCID 42633441, compound

HRID 2388245Notes

Reaction equation

HRID 2388245 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[C:12]([C:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=3)=[N:13][O:14][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].[O-]CC.[Na+].Cl>CN(C=O)C.O.CCOC(C)=O>[C:15]1([C:12]2[C:9]3[CH:10]=[N:11][C:6]([C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5])=[C:7]([OH:21])[C:8]=3[O:14][N:13]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 2723922Sodium ethoxideHCID 67530166HCID 67530166, compound

Product 1

HCID 42633441HCID 42633441, compoundYield 75.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Cyclohex-1-enyl-7-hydroxy-isoxazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (77 mg, 0.27 mmol) was dissolved in 10 mL of DMF. Glycine (0.40 g, 5.35 mmol) and sodium ethoxide (0.27 g, 4.01 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 60 mL of water. EtOAc (50 mL) was added and the resulting biphasic mixture was stirred vigorously as 4M hydrochloric acid was added dropwise until pH was 3. The aqueous layer was extracted with additional EtOAc, and the combined organic layer was washed with water and dried over MgSO4. The solvent was evaporated and the solid residue was taken up in 50 mL of saturated sodium bicarbonate solution. The aqueous phase was washed with hexanes and EtOAc. The aqueous layer was then acidified to pH 2 by addition of concentrated hydrochloric acid and the resulting precipitate was isolated by filtration to give 65 mg of the title compound. MS: (+) m/z 318.26 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. additionwas added dropwise until pH was 3
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. washThe aqueous phase was washed with hexanes and EtOAc
  8. additionThe aqueous layer was then acidified to pH 2 by addition of concentrated hydrochloric acid
  9. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-12b3bfa9d8d9437a91e3854bb073362b
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

Loading…